


As You Wish

by OliveBranched



Category: Supernatural
Genre: AU, Alternate Universe, M/M, Princess Bride!AU
Language: English
Status: Completed
Published: 2016-05-29
Updated: 2016-05-29
Packaged: 2018-07-11 00:58:41
Rating: Teen And Up Audiences
Warnings: Major Character Death
Chapters: 17
Words: 26,911
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7018276
Author URL: https://archiveofourown.org/users/OliveBranched/pseuds/OliveBranched
Summary: <blockquote class="userstuff">
              <p>Dean always wanted to live a quiet, simple life on his farm, away from the crowds and problems of the kingdom of Florin. When Dean's love goes out to sea and is killed by a notorious pirate, Dean suddenly finds himself betrothed to a prince and kidnapped and dragged across the countryside by a ragtag bunch of freelancers in a plot to start a war between Florin and Guilder, all the while pursued by a mysterious man in black who is rumored to be the pirate that killed Dean's love.</p>
            </blockquote>





	1. Prologue -- Farm Boy

**Author's Note:**

> This is more or less a rewrite of my earlier version of As You Wish that I let fall by the wayside in 2014. I decided this March that I wanted to finish it, but that I wouldn't publish any of it until I had every single chapter written, so I didn't have a repeat of what happened last time. I don't own Supernatural or The Princess Bride, or any of their characters, lines, and trademarks.

For as long as he could remember, Dean had lived on his farm. Florin was a beautiful country, the farm was prosperous, and Dean was happy. Every day he would ride his horse out into the surrounding fields, stop somewhere miles away where there was nothing around him but the open countryside, lay on his back in the grass and stare up at the sky. It was one of his favorite pastimes, second only to tormenting the young man that worked on his farm. Nothing gave Dean more satisfaction than ordering the man around. Dean didn't know his name; he just called him "Farm Boy."

"Farm Boy!" Dean's voice rang out through the stables as he dismounted his horse. The man's head popped up from behind the low wall separating the horse's stable from the cattle. The dark haired man looked at Dean patiently. "Polish my horse's saddle. I want to be able to see my face reflected in it tomorrow morning." The young man smiled.

"As you wish." Dean turned on his heel and strode back into his house. He loved the feeling he got from bossing the boy about, and hearing him answer so obediently. It sent a thrill down his spine every time the man's eyes locked with his own as he said: "As you wish."

"As you wish" was all that he ever said to Dean. No matter what he would ask of the man, his reply was always the same, those three words and that little smile. Dean began to ask more and more of the farm boy, things that he easily could have done. Still, the boy's reply never changed. Dean thought about asking the boy to leave and never come back, just to see what his answer would be, but quickly put the idea aside at the knots his stomach twisted into at the thought of losing him. He didn't focus too much on why he was so afraid of seeing him leave. 

Dean continued to torture the boy by asking him to find him an item of his clothing that he had purposefully hidden away, making him find a certain herb that he was missing for his supper, even telling the boy to muck out Impala's stable again because it wasn't clean enough, but the boy never wavered. He smiled and said "As you wish" before setting to work on the task he had been given. Though the young man been working for the farm since before Dean's father had gone away and Dean had taken over the farm, he had only just piqued Dean's curiosity. He cornered the boy in the stables one day.

"Farm Boy," Dean approached his crouched form as he tended to one of the cows. The man shifted onto one knee as he turned to look at him. Dean caught himself looking at the way the man's muscles shifted under his skin as he moved and he marveled at the pure strength in such a lean body. He forced himself to look back up at the man's eyes. "For all of the years you have worked here, I have never known your name." 

The man looked surprised for a moment before warmth returned to his face and Dean told himself that the man's smile wasn't any bigger than normal. 

"Castiel," the man said. Dean blinked once, twice, still lost in his thoughts.

"I'm sorry?" he said, and then mentally hit himself for the too-polite choice of words. 

"My name," the man told him, and for the first time, Dean noticed how blue his eyes were. "It's Castiel." 

"Castiel," Dean repeated. He smirked at him, then turned on his heels and left the stable, but not before he called out over his shoulder: "Don't forget to groom Impala, _Farm Boy_." 

If Dean were a liar, he would say that he had been too far away to hear Castiel say, "As you wish." And Dean was a wonderful liar.

Even though he knew Castiel's name, Dean continued to call him Farm Boy and assign him menial errands and chores, and he continued to be frustrated that Castiel's answer never changed. It puzzled and amazed him in ways that he did not understand. Almost a week later, Dean approached Castiel as he chopped firewood for the cold week ahead. 

Dean plopped the two large buckets down next to Castiel and was met with calm blue eyes that stopped his breath. Dean plastered a smirk on his face to hide that fact from Castiel.

"Fill these with water, Farm Boy," Dean ordered. Castiel stared at him, blue eyes expectant in a way they hadn't been before, and before he could stop himself, he heard his voice whisper, "Please?" Castiel smiled.

"As you wish." He went back to chopping firewood while Dean stood there, dumbfounded. He stared at Castiel for a few moments, completely floored by the sudden change. He had never made Dean ask for something nicely before. He straightened up and made his way back to his house. Dean stopped cold in his tracks, his hand frozen on the doornail when his mind finally put two and two together and came to the rational conclusion. 

Dean let himself inside and nearly collapsed into his chair at the table. His mind continued to shout its realization at him until he finally processed it. That day, Dean was amazed to discover that whenever Castiel had said, "As you wish," what he had meant was, "I love you." 

Dean stood up from the table as he heard Castiel come up the walk and enter the house. He looked at Dean as he walked in the door with a large pile of firewood and Dean swore he caught a mischievous sparkle in Castiel's eyes as he put the wood down by the fireplace.

Gods, Dean has no idea how he missed the love in those eyes before. All he knew was that it felt like his heart was about to beat its way out of his chest, his lungs were refusing to work, and his skin suddenly felt three sizes too small. Dean couldn't take his eyes off of how the muscles in Castiel's back rippled underneath his shirt as he stood up. He wanted to see more of him, all of him, to have those eyes look at him like that for the rest of his life. 

The force of Dean's revelation hit him square in the chest like a physical blow and knocked the wind out of him. Every time he had teased him, every time he had nearly gotten lost in his eyes, every time he had made the man stay inside his own home because it was too cold in Castiel's…how had he not known before? He watched as Castiel ran a hand through his hair, and not for the first time, he wondered what it would be like to run his fingers through that hair. He knew that he was staring and that Castiel would look back over at him any second, but Dean couldn't stop himself. His body was frozen while his mind ran a league a second. Dean was amazed to discover that he truly loved him back. Castiel turned to leave without so much as a glance at him and Dean almost tripped over his chair as he jumped to his feet. 

"Farm boy!" he called out. Castiel looked over his shoulder at Dean, hand still on the doorframe. Dean looked around for something, anything, any reason to make Castiel stay. He saw a pitcher hanging above his head. "Fetch that pitcher for me?" he asked. Castiel turned around and came closer until he was inches away. Castiel smiled and reached up to grab the pitcher, but his eyes never left Dean's. He held it out to Dean, and their fingers brushed as Dean accepted it. 

"As you wish," Castiel breathed, and Dean could feel trails of electricity left behind from where he and Castiel had touched. Dean gripped Castiel's hands as tightly as he could manage around the pitcher, and opened his mouth to say something, but no words came out. Castiel's smile grew wider, and Dean couldn't help but mirror it. Castiel extricated one of his hands from Dean's grip and moved it up to cup his face. Dean leaned into the touch and fought to keep his eyes open as Castiel leaned in and pressed their lips together. 

Dean wove his arms around Castiel's neck and sighed into the kiss as he ran his fingers through Castiel's hair. Castiel moved his hand to the back of Dean's head and scratched teasingly at his scalp before he smoothed the mussed strands of hair back down. Castiel's other arm wrapped around Dean's waist and pulled them closer together as he opened his mouth against Dean's. Dean groaned and tugged on Castiel's hair. Castiel hummed in pleasure and ran his tongue along the seam of Dean's lips. Dean sucked in a breath in shock and dropped the pitcher which smashed on the floor behind them.

The two men jumped back from each other at the noise but kept their arms wrapped around each other. Castiel glared at the remains of the pitcher, and Dean chuckled. Castiel turned his glare on Dean, but there was no real heat in it. Dean stroked his knuckles down Castiel's cheek and gave him a chaste kiss before he leaned back. Castiel's frown deepened when Dean stopped him from leaning in for more.  
"Help me clean this up?" Dean's eyes sparkled with mirth. Castiel smiled.

"As you wish."


	2. Prologue -- The Proposal

**Summary for the Chapter:**

> "Cas, can I…can I ask you something?" Dean began. Castiel tilted his head to the side and a confused frown stole across his face when he noticed Dean's serious expression. Castiel moved his hands from Dean's face to his shoulders and backed away so that he could look him in the eyes.

The days flew by after Dean finally admitted his feelings for Castiel. The two men grew closer with each passing moment. Dean took Castiel with him on his daily ride to the fields, and Castiel showed Dean his secret hideaway: a large cave by the river that ran through the forest. Dean still called him "Farm Boy" from time to time, but now it was an endearment rather than a cruel nickname. They had been together for nearly two months when Dean approached Castiel with an important question.

"Cas?" Dean called out as he entered their house. Castiel turned away from the fire and grabbed Dean's hand to pull him in for a kiss. Dean willingly knelt down to Castiel's level and wrapped his arms around his waist. Castiel smiled into the kiss and cupped Dean's face in his hands as he pulled away and rested their foreheads together. 

"Hello, Dean." He whispered and Dean could feel the words brush over his lips as they left Castiel's. Dean shuddered and Castiel's smile grew as he brushed his lips over Dean's. 

On any other day, Dean would have been content to lose himself in Castiel's kisses, but today he had other priorities. He reluctantly pulled back from the kiss and moved his hands to hold Castiel's wrists.

"Cas, can I…can I ask you something?" Dean began. Castiel tilted his head to the side and a confused frown stole across his face when he noticed Dean's serious expression. Castiel moved his hands from Dean's face to his shoulders and backed away so that he could look him in the eyes. 

"Of course, Beloved." Dean blushed and looked away at Castiel's use of the nickname. He took a deep breath and met Castiel's gaze. _Now or never_ , he thought to himself.

"Cas, will you marry me?" 

For several moments, the house was filled with shocked silence. Castiel's eyes were as wide as saucers and his mouth gaped open. Dean's stomach twisted into knots as he imagined the worst. 

"Dean, I…" Castiel trailed off. Dean sighed, and berated himself for asking so soon, then scooted away and started to stand up before Castiel's hand shot out and grabbed his wrist. Dean was surprised when he was pulled into a fierce kiss and his hands tangled in Castiel's hair almost as a reflex. Dean moaned into the kiss and eagerly parted his lips when Castiel ran his tongue along the seam of his mouth. When they broke off for air, Castiel's eyes sparkled and his smile lit up the entire room.

"Yes." He breathed out. Dean blinked in surprise for a few moments before Castiel leaned forward and gave Dean a chaste kiss. "Yes, I will marry you. I love you, Dean, and I would do anything for you. Anything you wish." He placed another kiss on Dean's lips, then tensed and pulled back. His eyes, which sparkled only a moment ago, were now shaded with unease. 

"What is it?" Dean noticed the change in Castiel's demeanor right away. "What's wrong?"

"If we are to be married, then I need to leave." Dean shook his head

"You…you what?"  
"I have to go and seek my fortune in the world." Dean would have laughed at Castiel's typical blunt phrasing if his heart hadn't felt like it was breaking in two.

"'Seek your fortune?' Cas, that's ridiculous. I don't care about any of that fancy crap. As long as you're here, I can be happy." Dean pleaded. Castiel shook his head.

" _I_ care, Dean. I want to give you the best of everything, and to be able to do that, I have to leave." Dean grabbed Castiel's shoulders.

"No, you don't! I'm telling you, Cas, I just want you. Nothing else matters to me but having you here with me." Castiel placed his hands over Dean's and rubbed his thumbs over the backs. 

"I know, Dean. Really, I do, but this is important to me. It's something I have to do." Dean stepped away from Castiel furiously, determined to keep himself from crying.

"Why? Why is it so important to do something that would take you away from me?" Castiel didn't try to get any closer to Dean, he just stood there and stared at him with mournful eyes.

"Because you deserve so much better, Dean, and I want to be that for you." Dean's hands clenched into fists at his side.

"Cas, please don't leave. Please." Castiel didn't reply, just stood there with his eyes fixed on Dean, and his expression gave Dean his answer. Dean nodded his head sharply and blinked back the tears that had gathered. 

"I really can't convince you to stay, can I?" Dean phrased it as more of a statement than a question and Castiel answered with a small shake of his head. When he saw the desolate look on Dean's face he hurried closer to him and took both of Dean's hands in his own.

"Dean, this isn't forever. I promise I won't be long." Dean squeezed his hands.

"When will you go?" Dean tried and failed to keep the tremor out of his voice. Castiel rubbed his thumbs over the back of Dean's hands.

"Charlie's trade ship leaves for Guilder at noon tomorrow. I can be ready by then." Dean gripped even tighter to Castiel's hands. Castiel released Dean's hands so that he could wrap his arms around Dean and pull him close to his body, while Dean's arms wrapped tightly around his neck as if he could make Castiel stay if he held tight enough. After a few moments, Dean moved back so that he could look into Castiel's eyes.

"If you're leaving tomorrow, then you should pack now. You wouldn't want to miss your ship, would you?" Dean smiled at him, but Castiel could hear the sorrow in his voice. Castiel leaned forward and sealed their lips together. When they pulled away, Castiel pretended not to notice the tears in Dean's eyes, just as Dean pretended not to notice those in Castiel's. After they had finished packing Castiel's few belongings, the two men lay down in their bed and curled around each other tightly before they drifted off into a fitful sleep. 

\---OoO---

The morning came. Castiel had collected his things and was prepared to leave. He wrapped Dean in his arms and held him close. Both of them held back tears. 

"I'm afraid that if you leave, we'll never see each other again," Dean confessed into the side of Castiel's neck. He felt Castiel smile and clutch him tighter. 

"Of course, we will." Castiel's hands stroked comfortingly up and down Dean's back as he spoke. 

"But what if something happens to you?" Castiel's hands stilled their ministrations and he pulled back to lock eyes with Dean.

"Listen to me: I will always come for you." Dean took in a deep shuddering breath and raised a hand to cup Castiel's cheek.

"How can you possibly be sure?" Castiel smiled at him and brushed his lips over Dean's.

"This is true love," Castiel replied, his voice steady and sure. "Do you think this happens every day?" Dean let out a watery laugh as Castiel pulled him in for a long, lingering kiss before he pulled away completely. Dean watched helplessly as Castiel picked up his bag and gave Dean one final kiss before he turned away and left their farm. 

\---OoO---

Dean waited weeks for any word from Castiel. He had assured Dean before he left that he would write as often as he could, but Dean had not received a single letter. Almost two months had passed before Dean finally found a single letter waiting for him on his doorstep when he returned from his daily ride. 

He was so eager to hear from Castiel that he didn't notice that the seal was far too formal to be anything from Castiel, or that the handwriting in the letter was too neat to be Castiel's messy scrawls. He broke the seal on the letter, unfolded it and read.

_Dear sir,  
We wish to express our deepest condolences on your behalf in regards to your servant on this farm. He recently departed for Guilder on the Ariel. We regret to inform you that your servant did not reach his destination. The Ariel was attacked by the Dread Pirate Roberts and the whole of the Ariel's crew and its passengers were slaughtered. We send our sincerest apologies._

_Admiral West of Florin's Naval Forces_

Dean's mind went blank. What he had read could not be correct. There had to be some mistake. He read it three more times for good measure, certain that the letter had been meant for someone else, but he was unable to avoid what his mind already knew for very long.

Dean sank into his chair by the fire, completely numb. Once his body had caught up with his mind he buried his face in his hands and let himself come apart. He didn't know when or how, but he eventually ended up on his knees in front of the fire, with the coat that Castiel had left behind clutched in his hands as he breathed in the familiar scent of his soap and skin. 

When the wracking sobs subsided and Dean's breathing had returned to a normal rate, the sun had already set and it was pitch dark outside his house. Dean winced as he stood up on his stiff legs and dragged himself over to his bed where he collapsed, with Castiel's coat still in his hands as he slipped into a sleep plagued by nightmares of Castiel being brutally murdered by the Dread Pirate Roberts.


	3. Five Years Later

**Summary for the Chapter:**

> Dean stepped forward into the horde of people, who dropped to their knees as he passed them. Many of them reached out to brush their fingers against his clothes, some going so far as to outright grab at him. Dean gently brushed them off and continued through the throng of villagers. He didn't stop to look too long at any of them. He carefully made his way past awestruck eyes and grasping hands to reach the stone staircase that lead up to Michael's balcony.

Five years later, the entire kingdom of Florin was in a state of excited chaos as they hurried to finish their preparations for the upcoming festival that would accompany Prince Michael's announcement of his betrothed. All of Florin was anxious to discover who had been chosen to marry Michael. The older citizens gossiped amongst themselves that it was about time that he was married, while the children and young adults reveled at the thought of a kingdom-wide celebration. 

Trumpets blared out across the packed square to announce the arrival of the royal family on a balcony high above the crowd. Lucifer, Michael's second-in-command, was the first to emerge, followed by King Charles and Queen Rebecca, and finally, Michael himself, his crimson attire caught the eye of everyone below and brought the crowd to a hush as Michael stepped forward.

"My people," he intoned, voice imperious and booming. "One month from now, our country will have its five hundredth anniversary. That evening, I shall marry someone who was once a commoner, like yourselves. But, perhaps you will not find him common now." Michael smirked as he looked over to where his betrothed would appear. "Would you like to meet him?" The crowd chorused their approval, and Michael raised his hand to quiet them again. 

"Very well then. My betrothed, Prince Dean." Michael gestured across the square to the castle gates, which slowly opened to reveal a stunningly handsome young man, dressed entirely in white silks, distinguished by a simple gold circlet around his forehead. 

Dean stepped forward into the horde of people, who dropped to their knees as he passed them. Many of them reached out to brush their fingers against his clothes, some going so far as to outright grab at him. Dean gently brushed them off and continued through the throng of villagers. He didn't stop to look too long at any of them. He carefully made his way past awestruck eyes and grasping hands to reach the stone staircase that lead up to Michael's balcony. 

Dean could feel the eyes of the villagers on him as he climbed the stairs to stand at Michael's side. As soon as Dean was within reach, Michael wrapped an arm around his waist and tugged him into his side. Dean stumbled but did not resist. From the instant Michael had laid eyes on Dean and declared him his chosen spouse, the man had insisted on publicly displaying his affection for Dean, who had vehemently protested at first, but soon discovered that the stubborn prince would do what he wanted, regardless of Dean's wishes. 

The whole ceremony lasted for another two hours, with performances from musicians and dancers and a traveling circus that had come through Florin and was invited to the celebration. The villagers laughed and cheered while Dean watched them from his perch on the balcony, held firmly at Michael's side. When the festivities were finally over, Dean quickly excused himself, shed the ornate clothes specially made for the celebration in exchange for a simple red tunic and brown pants. He peeked into the hallway outside of his chamber to ensure that no one would see him leave, and then hurried to the stables where he mounted Impala and rode off into the Thieves' Forest. 

For the two months that Dean had been living at the castle, he had been sequestered away into his small chamber, only allowed to leave for meals and when Michael would summon him for some small whim or other. The only time that Dean felt he truly had to himself were the few hours a day he managed to steal with Impala. Out in the forest, he didn't have to be _Prince Dean, Michael's Betrothed_. He could disappear and just be Dean, if only for a little while. It was the only time that Dean ever really felt free.

Today, however, Dean felt uneasy. He shook it off and blamed it on all the time spent beside Michael prior to his ride. The feeling returned full force when he reached the thickest part of the forest and came upon three men standing shoulder to shoulder, blocking his path. Dean gently pulled Impala to a halt about ten feet away from them and stayed put to survey the three men.

The one on the left was a short, greasy looking guy with a suspicious glint in the gaze that he had fixed on Dean. Dean shuddered and looked over at the other two people. The one in the middle was tall and muscular, with an impressive looking sword hanging at his side. This one wouldn't meet his gaze, and Dean could see that he kept his eyes fixed on the ground. Dean ignored this and moved his gaze over to the man on the right, and his eyes nearly popped out of his head. This man was _enormous_. Dean figured he had to be at least seven feet tall, probably taller, and he was built like a human boulder. The giant's gaze seemed to take everything in with rampant curiosity and never stayed in one place for very long. Intrigued, Dean cautiously urged Impala closer, and stopped again when the short one called out to him.

"A word, my lord?" he asked. Dean nodded for him to continue, and he bowed his head in thanks, though the gesture seemed to be more sarcastic than respectful. "We are but poor, lost circus performers," the man continued, head still bowed, then lifted his eyes to lock onto Dean's. "Is there a village nearby?" He asked, and the glint returned to his gaze. Dean suppressed his shudder this time and pressed on.

"Sorry, but you're out of luck. There's nothing around for miles." The short man grinned and the look in his eyes turned predatory. Dean's blood ran cold.

"Then there won't be anyone around to hear you scream," he said, more for his sake than for Dean's. Dean opened his mouth to scream but was quickly silenced when a massive hand clamped down where his neck became his shoulder and squeezed hard. He managed to turn his head to see the giant right next to him, pulling his limp body off of Impala while his hand stayed locked on his neck. Within seconds, Dean was unconscious.

\---OoO---

Crowley chuckled under his breath as the Princeling collapsed into Benny's arms. He motioned for the two men to follow him and set off through the forest to their ship. He jerked his head at Benny and pointed at the ship. The giant lumbered up the dock and onto the ship with Dean still limp in his grasp. 

Crowley then grabbed a cloak out of his satchel and began to rip the coat of arms off of the front. The taller man noticed from the bow of the ship and called down to Crowley. 

"What are you ripping?" he inquired. Crowley rolled his eyes and muttered an insult at the man, too quietly for him to hear.

"It's fabric from the uniform of an army officer of Guilder," he replied tersely but didn't look up from the cloak. 

"Who's Guilder?" a deep voice boomed from the deck. Crowley stifled a growl at the giant's idiotic question. He took a moment for himself to lament choosing uneducated fools as his company.

"The country across the sea?" Benny raised an eyebrow at him. "The sworn enemy of Florin?" The other eyebrow came up. He finished his work and firmly attached the coat of arms to the horse's bridle and swatted its flank to send it running back towards the castle. He stormed up the dock and leveled a glare at Benny. 

"Once the horse reaches the castle, the fabric will make the Prince suspect that the Guilderians have abducted his love. When he finds his body dead on the Guilder frontier, his suspicions will be confirmed." Benny gently propped Dean up against the side of the ship and turned his solemn gaze to Crowley, the first flickers of apprehension entering his eyes. 

"You never said anything about killing anyone."

"I've hired you to help me start a war! It's a prestigious line of work, with a long and glorious tradition." Benny maintained his intense stare.

"I just don't think it's right, killing an innocent man." Crowley narrowed his eyes at him and stalked forward.

"Am I going mad, or did the work _‘think'_ escape your lips? You were not hired for your brains, you hippopotamic land mass!" The taller man leaped over the edge of the ship from where he had been removing the dock and landed on the deck.

"I agree with Benny." Crowley sneered. 

"Oh, the sot has spoken!" Crowley reveled in the man's visible flinch at the name. "What happens to him is none of your business. _I_ will kill him, and remember this – _never forget this_ – when I found you, you were so slobbering drunk you couldn't buy brandy!" Crowley rounded on Benny and advanced on him until he was practically standing on the giant's toes, his head almost completely leaned back so that he could look at his face. "And _you_. Friendless, brainless, helpless, _hopeless_! Do you want me to send you back to where you were? Unemployed in _Louisiana_?" With his tirade over, he stomped down the stairs into the cabin and slammed the door behind him. 

Sam Winchester waited until he heard the door slam, then stood up and walked over to where Benny was preparing the sails. He pushed his long hair out of his face and reached up to pat Benny on the shoulder reassuringly. 

"That Crowley, he can _fuss_ ," Sam prompted, and shot Benny an expectant look.

"Fuss, fuss…" Benny mused. He looked down at Sam. "I think he likes to scream at _us_." Benny accentuated the rhyme through his thick Cajun drawl. Sam grinned.

"He probably doesn't mean any _harm_." 

"He's very, very short on _charm_." Sam laughed and paced over to the side of the ship. He shook his hair back out of his face as he leaned against the wooden railing. 

"You really know how to rhyme!" Benny smiled. 

"Some of the time." Crowley emerged from the cabin just as Benny completed his latest rhyme, and growled in frustration. 

"Enough of that!" he snapped. Sam rolled his eyes and peered ahead as the ship began to move away from the docks.

"Hey Benny," he asked, a conspiratory smirk plastered over his face. "Are there rocks ahead?" 

"If there are, we'll all be dead!" Benny bantered back. 

"No more rhymes now, I mean it!" Crowley hissed. Sam and Benny exchanged a look, and Sam nodded.

"Anybody want a peanut?" Crowley roared in frustration, as the ship sailed out into open waters.


	4. The Shrieking Eels

**Summary for the Chapter:**

> Crowley slowly approached Dean and crouched in front of him. Dean leaned away, but Crowley grabbed his wrists to force him closer. “I bet you think you’re brave, don’t you?”
> 
> “Braver than you.” Dean returned, and Crowley’s nostrils flared before he stomped away and left Dean alone.

Dean awoke hours later propped up against the side railing of a ship with his bound hands resting in his lap. He took in his surroundings and saw the smarmy-looking man standing directly across from him, but his gaze was focused elsewhere. He turned his head to look at the other end of the ship and saw the youngest of the three men staring off into the distance. Dean fought back a laugh when he shook his head like a horse to get his long hair out of his eyes. Dean allowed his own gaze to drift until he locked eyes with the goliath, who stood on the stairs, his eyes never leaving Dean’s. Dean made a shocked sound under his breath, and Smarmy looked over at him.

“Ah! The beauty awakens. How are you feeling, Highness?” Dean’s lip curled at the obvious distaste in Smarmy’s tone. 

“Just peachy, thanks. Wanna tell me where we are?” Dean growled. Smarmy raised his eyebrows in mock surprise. 

“I’m amazed, Highness. I would have thought, in all your time as Prince Michael’s little bitch that you would have seen a ship before.” Dean flinched, and dug his nails into his palms at the insult. Smarmy laughed. “You’ll see soon enough. We’ll reach the cliffs by dawn.” 

Dean quickly took inventory of all the cliff areas he knew of that were accessible by nearly a day’s journey from Florin. Unfortunately, there were many, and they could be headed towards any of them. Dean tried to angle his body to get a better view of the ships’ surroundings to see if there were any visible landmarks, but all he could see for miles was water. Dean was roused from his thoughts by Smarmy shouting at the young man. 

“Why do you keep doing that?” He shouted, annoyance clear in every line of his body. Dean managed to look at Hairy in time to see him peering over the edge of the ship before he turned to face Smarmy. He shrugged.

“I’m making sure no one’s following us.” Smarmy gave him a scathing look.

“That would be inconceivable,” he deadpanned. Hairy just huffed and turned back to keep watch.

“This’ll never work, you know. You’re gonna get caught.” Dean jutted his chin out at Smarmy. “And when you do, the Prince will see you all hanged.” It turned his stomach to think of asking Michael to do something like that for him, but he knew without a doubt that the man would do it in a heartbeat. 

“Of all the necks on this boat, _Highness_ ” Smarmy spat. “You should be worrying about your own.” Dean swallowed and turned his attention back to Hairy, who seemed to be fascinated by something over the side of the ship. Smarmy noticed and groaned. “Stop doing that!” He snapped. “We can relax. It’s almost over.” He shot a look at Dean that made his blood run cold. 

“You’re sure no one’s following us?” Hairy pressed.

“I told you, it would be absolutely, totally, and in all ways, _inconceivable_.” Hairy stared at him. “Nobody in Guilder knows what we’ve done, and nobody in Florin could’ve gotten here so fast!” he insisted, then sagged into a stool across from Dean and thunked his head hard against the railing. 

He sat there, eyes closed and motionless apart from his steady breathing, for several seconds before he jolted upright and looked over at Hairy.

“Just out of curiosity, why do you ask?” There was an edge of cautious fear to his voice that hadn’t been there before. Dean reveled that even this unshakeable man could be moved. 

“Because I happened to turn around, and something’s there.” Hairy replied casually. Smarmy leaped up from his seat and raced over to join Hairy at the edge of the ship. Dean took a moment to laugh at how he had to stand on his tiptoes to see over the edge of the railing. 

There was another boat visible on the water, Dean could just barely make it out from his vantage point on the lower part of the deck. He looked over at Colossus and noticed that he too had joined the other men at the railing. Dean saw his opportunity and took it. Moments like these were when he thanked the Gods that his father had taught him how to undo any knot he came across.

“It’s probably just a local fisherman out for a pleasure cruise…at night…through eel-infested waters…” Smarmy didn’t sound convinced and neither did Hairy or Colossus. Dean gave an internal shout of triumph as the knots gave way and the ropes slid easily off his wrists. He quickly grabbed hold of the railing, hoisted himself over it and dropped into the water below.

\---OoO---

The three men turned abruptly at the sound of a splash nearby. Crowley looked to where they had left the lordling, only to find him gone. He turned his gaze to where the splash had come from and watched as Dean swam further away from the ship. He rounded on the other two men.

“Go, you prats!” He roared. Sam and Benny both gave him matching blank stares. “Get in! Go after him!”

“I can’t swim,” Sam looked more nonchalant than embarrassed.

“I only dog-paddle,” Benny stared at Crowley who screamed in fury and rushed to the side of the ship where he could see Dean. 

“Veer left!” he yelled at Sam, who trudged over to the ships wheel and spun it the opposite way. “ _Left_!” he raged, and this time, Sam complied and the ship sailed into Dean’s path. As Crowley watched their most valuable asset swim further and further away, he began to hear a distant cry. A grin broke out on his lips as Dean stopped in his tracks and looked around for the source of the cries. 

“Do you hear that? Know what that sound is, Highness? Those are the Shrieking Eels!” Dean whipped around to look at Crowley, whose smile was only getting wider by the second. “If you don’t believe me, just wait! They always grow louder when they’re about to feed on human flesh!” He relished Dean’s panicked gasp as the spinal ridge of one broke the surface dangerously close to him. This was Crowley’s chance to save this whole endeavor. 

“If you swim back now, I promise that no harm will come to you. I doubt you’ll receive such a generous offer from the eels.” He bargained. He watched as Dean twisted and turned in the water to keep all of the eels in his sight, but there were too many. Crowley nodded at Benny as one snuck up behind him to take a bite out of Dean’s head. 

Dean turned at the last second to see the eel, and tossed his arms up as a last defense, but no attack came. He lowered his arms just in time to feel himself being grabbed roughly by the shoulders and hauled back over the railing onto the ship. 

“I think he’s getting closer!” Sam called out, and Crowley rounded on him. 

“He’s no concern of ours,” Crowley hissed. “Sail. On.” Crowley slowly approached Dean and crouched in front of him. Dean leaned away, but Crowley grabbed his wrists to force him closer. “I bet you think you’re brave, don’t you?”

“Braver than you.” Dean returned, and Crowley’s nostrils flared before he stomped away and left Dean alone. A sudden gust of wind hit Dean and he shivered. Sam noticed and fetched a blanket from below deck. He approached like Dean was a skittish foal.

“Take this,” he handed the blanket over. Dean turned his head away stubbornly. “You’ll catch a cold if you don’t use this.” Dean still resisted and Sam sighed, then tossed the blanket at Dean’s feet and bit out a “you’re welcome” before he returned to his post. 

Dean watched him leave before he wrapped the blanket around himself. He scanned the deck for any sign of Crowley before he let his guard down and drifted off into a fitful sleep.


	5. The Cliffs of Insanity

**Summary for the Chapter:**

> Dean was shocked. Never had he met anyone that could climb something this high that quickly. He briefly entertained the thought of it being someone sent to rescue him, but stopped that fantasy in its tracks almost immediately. It just wasn’t possible.

Dean was rudely awoken by a sharp kick to his side. He opened his eyes to see Smarmy looming over him, trademark sneer pasted on his face. Dean glared and pulled himself into a sitting position. He forced himself not to wince when his side twinged in pain. 

“What?” Dean spat. 

“I’d be more careful with how you speak to me, Highness. Remember, it’s up to me how I kill you. If you behave, I just might make it quick. If not…well, let’s just say you’d rather behave.” Dean opened his mouth to respond but was cut off by Hairy.

“Look! He’s right on top of us!” Dean glared at Smarmy’s back as he stalked over to the end of the ship. He craned his neck to see around the two men, and just barely managed to get a glimpse of the rapidly gaining ship before Colossus moved to look as well and completely obstructed his view. “I wonder if he’s using the same wind we’re using…” Hairy mused as he adjusted the sails. 

“Whoever he is, he’s too late!” Smarmy announced dramatically and pointed straight ahead. “See? The Cliffs of Insanity!” Dean’s head whipped around to look and saw what had to be the highest cliff face in the world. Dean gulped as he pondered all of the horrible ways to die on those cliffs. “Hurry up!” Smarmy’s voice interrupted his gruesome thoughts as he barked orders to the other two men. 

“Move the thing!” He shouted in Colossus’s face.” And that other thing!” He aimed at Hairy, who shot a glare at Smarmy when he wasn’t looking. “Move it!” He continued to scream as the ship stopped directly adjacent to the cliff face. Colossus jumped out of the ship onto a small ledge at the bottom of the cliffs and fiddled with a length of rope that dangled down from the top. Smarmy checked the surrounding area and noticed the other ship circling around the narrow entrance they had taken.

“We’re safe! Only Benny is strong enough to go up our way. He’ll have to sail around for hours until he can find a harbor!” As he spoke, Benny lifted Dean over the railing of the ship and placed him down on the ledge next to him, then donned a black leather vest with three harnesses on it, one which he attached to Dean, the other two he handed to the men, and the fastened them on. Hairy checked over Dean’s harness before he nodded at Benny, who grabbed the rope and began to climb. 

Once they started their ascent, Dean made the mistake of looking straight up at the cliffs. The sheer height was dizzying. He closed his eyes and gripped tighter to Benny in fear. He thought of anything and everything that would keep his mind off of the climb, his mother, his horse, Michael, _anything_. He was desperate. Dean figured they must have been halfway up the cliff when Hairy looked below them and made a shocked noise.

“He’s climbing the rope.” He said, disbelief clear in his tone. “And he’s _gaining_ on us.” He added as the figure grew closer. 

“Inconceivable.” Smarmy mocked, before he, too, looked down and watched as the man in black swiftly made his way up the rope. Dean was shocked. Never had he met anyone that could climb something this high that quickly. He briefly entertained the thought of it being someone sent to rescue him, but stopped that fantasy in its tracks almost immediately. It just wasn’t possible. 

“Faster!” Smarmy shouted in Benny’s face.

“I thought I was going faster,” Benny replied in what Dean had decided was his typical monotone. 

“You were supposed to be this Colossus. You were this great, legendary thing, and yet he _gains_!” Crowley spat. Benny didn’t even flinch and Dean was relieved that his pace never wavered.

“I’m carrying three people, and he just has himself.” 

“I’m not looking for _excuses_! I guess I’ll have to find myself a new giant.” Benny quirked an eyebrow, which seemed to incense Smarmy even further. “Did I make it clear that your _job_ is at stake‽” Benny increased his pace only slightly, but within seconds, they had reached the top of the cliffs. 

Dean yanked off his harness and collapsed against a rock. He could’ve kissed the ground in relief, but he managed to keep himself from doing anything more than pant heavily against the rock. Smarmy rolled his eyes, pulled a dagger from his belt and began to saw at the rope where it was tied around a boulder. Dean watched in horror as the rope frayed, then snapped and slid off the edge of the cliff into the waters below. The three men raced to the edge of the cliff and peered over to see if the man in black had fallen too. Instead, they spotted a dark figure clinging to the ledge. 

“He’s got very good arms,” Benny commented. 

“He didn’t fall? Inconceivable!” Smarmy stomped his foot and Dean had to stifle a laugh at how much the action made him look like a child throwing a tantrum. Hairy turned to stare at him.

“You keep saying that. I don’t think it means what you think it means.” Smarmy levelled a glare at him that could have frozen molten lava. Hairy shrugged his shoulders and returned his attention to the man in black, who had begun to inch his way up the cliff. “Oh my God. He’s climbing.” 

“Whoever he is, he’s obviously seen us with the Prince, and therefore, must die. You—“He jerked his head at Benny. “Carry him.” Benny nodded and ignored Dean’s protests as he hoisted him up over his shoulder. Benny seemed to have the patience of a saint while he stood motionless as the smaller man to beat his fists against him while he waited. “You catch up with us when he’s dead. If he falls, fine. If not, the sword.” Hairy smirked.

“Fine. But I’m going to duel him left-handed.” Smarmy rounded on him, eyes ablaze. 

“You know what a hurry we’re in!” Hairy shrugged and gave him a faux-innocent smirk. 

“It’s the only way I can be satisfied. If I use my right, then it will be over too quickly.” 

“Fine. Have it your way.” Smarmy huffed, and headed up the path around the bend. Benny set Dean down on a stone step and gave him a look that told him exactly what would happen to him if he tried to run. Dean’s eyes widened, but he stayed put. 

“You be careful,” Benny told Sam. “People in masks can’t be trusted.” Sam smiled at him and nodded. Crowley stomped back around the bend.

“I’m waiting!” Benny clapped Sam soundly on the shoulder which sent him stumbling forward a few steps, then hefted Dean up over his shoulder again, but this time with Dean’s hands trapped against his chest, and followed Crowley up the path. 

Sam watched until they were completely out of sight and Dean’s shouts of threats and obscenities faded into the distance, then walked back to the ledge and peered over.

“Hey there!” The man in black squinted up at him and tilted his head to one side like a bird. “How’s it going?”

“Look, I don’t mean to be rude, but this isn’t as easy as it looks, so I would appreciate it if you wouldn’t distract me.” The man in black rasped out, slightly breathless from climbing. 

“Sorry.” Sam held up his hands in surrender and backed away from the ledge.

“Thank you.” Sam paced for a few moments, ran through a few cuts with his left hand, then sheathed his sword and returned to the ledge.

“I don’t suppose you could hurry it up a bit?” He asked. 

“If you’re in such a hurry, you could lower a rope or a tree branch or find something useful to do.” Sam laughed. 

“I could do that.” He gestured to the length of rope that remained wrapped around the boulder. “I do have some rope up here, but I don’t think you would accept my help since I’m really just waiting around to kill you.” The man in black stopped fidgeting on the ledge.

“That does put a bit of a damper on our relationship.” Again, Sam laughed at the man’s deadpan sense of humor. 

“I can promise that I won’t kill you until you reach the top.” Sam offered. This time, it was the man in black who chuckled.

“That’s very comforting. But I’m afraid you’ll just have to wait.” 

“I hate waiting.” Sam stepped away from the ledge then immediately stepped back. “Could I give you my word as a Winchester?” The man in black went very still.

“A what?” Sam rolled his eyes.

“A Winchester. It’s my family name.” The man in black nodded.

“No good!” The man grunted as rocks crumbled beneath his foot and he quickly adjusted to keep himself from falling. “I’ve known too many Winchesters.” Sam wasn’t in such a hurry that he didn’t catch the hint of sorrow in his voice.

“Is there any way I can get you to trust me?” 

“I can’t think of anything.” Sam was about to give up and let the man fall when he thought of exactly what to swear by. 

“I swear on the sword of my father, John Winchester, you will reach the top alive.” The man in black hesitated for a moment, eyes locked on Sam’s.

“Throw me the rope.” Sam grinned and uncoiled the rope just enough so that it brushed the man in black’s fingertips. He grabbed onto the end and hoisted himself up the rope as Sam pulled it up from his side. When he was close enough, Sam reached down and grabbed the man in black’s hand to pull him up the rest of the way. 

“Thank you.” The man in black said to Sam, then reached for his sword.

“No, no!” Sam stopped him. The man in black looked at him in confusion, his head doing that strange bird-like tilt again, “We’ll wait until you’re ready.” The man in black relaxed.

“Again, thank you.” He said as he limped over to a flat topped boulder. He sighed out when he sat, took off his shoes and turned them upside down. Sam winced when a shower of rocks tumbled out.

“I don’t mean to pry,” Sam began, and the man in black looked up at him. “But you don’t happen to have six fingers on your right hand, by any chance?” The man in black stopped. 

“Do you start all of your conversations like this?”

“My father was murdered by a six-fingered man.” Sam explained. The man lifted up his right hand and wiggled all five fingers. Sam laughed nervously. “He was a great sword maker, my father. The six-fingered man came to him and requested a special sword. My father took the job. He slaved over it for a year before it was finished.” Sam drew his sword from the scabbard and held it carefully, reverently in both hands. He held it out to the man in black, who took it and looked it over. 

“I have never seen its equal.” He handed the sword back to Sam, who almost seemed to cradle it in his hands as he spoke.

“The six-fingered man returned and demanded it – but at one tenth of his promised price. My father refused. Without a word, the six-fingered man slashed him through his heart.” Sam sheathed the sword and looked the man in black in the eyes. “I love my father. So, naturally, I challenged his murderer to a duel.” He laughed self-deprecatingly. “I failed. The six-fingered man left me alive, but he gave me these.” Sam gestured to two jagged scars on his cheeks, and the man in black winced in sympathy. 

“How old were you?”

“I was eleven years old.” The man in black nodded gravely. “When I was strong enough, I dedicated my life to the study of fencing, so that the next time we meet, I won’t fail.” Sam’s eyes grew determined. “I will go up to the six-fingered man and I will say, ‘Hello. My name is Samuel Winchester. You killed my father. Prepare to die.’” 

“You’ve done nothing but study fencing?” 

“It’s been more of a pursuit than a study, lately.” Sam seated himself next to the man in black. “You see, I can’t find him. It’s been twenty years now, and I’m starting to lose confidence. I’m only working for Crowley to pay the bills. There’s not a lot of money in revenge.” The man in black hummed in agreement, then both men were silent for a few moments before the man in black stood up and dusted himself off. 

“Well, I certainly hope you find him someday.” He told Sam earnestly. 

“You’re ready, then?” The man chuckled. 

“Whether I am or not, you’ve been more than fair.” The two men unsheathed their swords.

“You seem like a decent man. I hate to kill you.” Sam told the man in black, half-joking.

“You seem like a decent man. I hate to die.” Sam grinned and nodded at him.

“Begin.”

Sam moved into his en gardé and carefully catalogued every aspect of the man in black’s movement. Sam struck first, two cuts easily parried by the man in black, follow by a swipe to the head, which he evaded. They circled each other, and when Sam struck again the man in black parried and followed it up with a swipe of his own. Sam ducked out of the way, the blade barely grazed the ends of his hair as it passed over his head. Then the duel began in earnest. 

Both men attacked and parried swiftly and confidently, their advances and retreats as natural as breathing to both of them. Sam bound the man in black’s sword off, then swiped at his head, but the man dodged away with ease. 

“You’re using Bonetti’s defense against me, then?” Sam asked over the clang of their blades.

“I thought it fitting, considering the rocky terrain.” The man in black smirked, even as Sam backed him up a set of stone steps.

“Naturally.” The man in black leapt up the last two stairs without so much as a glance behind, all the while his blade struck out against Sam’s. “You must expect me to attack with Capo Ferro!” 

“Naturally, but I find that Thibault cancels out Capo Ferro.” The man in black dodged another swipe at his head. “Don’t you?” He leapt off the edge of the stairs and landed on the ground below. 

“Unless the enemy has studied his Agrippa.” Sam jumped off of the ledge, flipped over the man in black, and landed opposite him in en gardé. “Which I have!” Sam grinned, and the two men resumed their duel. The man in black advanced on Sam, which forced him to retreat towards the path Crowley and Benny had taken. Sam couldn’t let the man in black get to them, he had to create a diversion.

“You’re wonderful!” Sam baited.  
“Thank you.” The man in black remained calm, and Sam was astonished that he wasn’t showing any signs of exertion even though Sam was already beginning to get winded. “I’ve worked hard to become so.” 

“I admit it,” Sam lunged at the man in black, who side stepped him. Sam quickly turned back around to face him. “You’re better than me.” 

“Then why are you smiling?” The man in black asked as he back Sam up to the cliff’s edge.

“Because I know something you don’t know.” Sam hoped to throw him off his guard. Unfortunately, it didn’t work as the blows kept raining down on Sam.

“What’s that?” The man asked and Sam grinned even wider.

“I’m not left handed!” Sam hastily switched to his right hand and pushed the man in black up the steps to a higher ledge near a crumbling archway with a simple wooden bar as the only thing that held it together. Since he switched hands, he had easily gained the upper hand, managed to knock the man in black off his feet on the stairs, and land a few small cuts on his legs before he regained his footing. 

“You’re amazing.” The man remarked, unfazed.

“I hope so after twenty years!” He pushed the man in black further up the ledge until he had him pinned against a stone wall. 

“There’s something I think I should tell you.” The man ground out, and now Sam noticed that his breathing was slightly raspy from being pressed against the stones. 

“What’s that?” Sam asked, and for that one second, he let his guard down and released the pressure just enough for the man in black to shove him away.

“I’m not left handed either.” The man in black elaborately tossed the sword from his left hand to his right, twirled it around and exchanged a few blows with Sam before the man in black managed to disarm him and sent his sword flying away. He forced him to retreat down the top few stairs before Sam looked behind himself and saw the wooden bar. He quickly grabbed onto it and jumped down onto the lower level, then grabbed his sword from where it had fallen. 

Sam looked up just in time to see the man in black toss his sword at the ground, where it stuck perfectly into a patch of moss by Sam’s feet. The man in black then jumped onto the same bar, flipped over the bar, then landed easily on his feet in front of Sam and retrieved his sword from the patch of moss. Sam stared at the man, completely bewildered. 

“Who are you?”

“No one important.” The man replied, coolly. 

“I have to know.” The man gave him a pitying smile.

“Get used to disappointment.” Sam shrugged, then lunged at the man, who parried each of his blows and pushed him further and further back towards the path leading to Crowley and Benny. He knocked Sam’s blade out of his hands up into the air and pushed him back a few more steps, where Sam caught it out of the air and resumed thrusting at the man. 

The man in black forced Sam to retreat all the way to the arch separating them from the path, smoothly dodged two more swipes from Sam, then twirled his sword rapidly around Sam’s face before he swiped at his hair, which startled Sam enough to make him drop his sword. Sam dropped to his knees as the man in black paced around to stand behind him, sword pointed at his throat.

“Kill me quickly.” Sam begged. The man behind him laughed.

“I would rather destroy a stained-glass window than an artist like yourself.” Sam relaxed visibly. “However, since I can’t have you following me…” The man in black struck Sam soundly across the head with the hilt of his sword. Sam collapsed onto the ground in front of him.

“Please understand, I hold you in the highest respect.” Then Sam blacked out entirely.


	6. The Man in Black vs. Benny

**Summary for the Chapter:**

> “Pick up one of those big rocks and hide behind that boulder. In a few minutes, the man in black will come running around the bend. The minute his head is in view, hit it with the rock!” he shouted, then stormed down the path and out of sight.
> 
> “My way’s not very sportsmanlike.” Benny reflected as he picked up one of the large rocks at his feet and crouched behind the boulder.

“Inconceivable!” Crowley raged as he watched the man in black emerge from the archway and jog up the path towards them. He turned to face Benny. “Give him to me. Catch up with us quickly!” No sooner had Benny set Dean on his feet than Crowley had grabbed his wrist and begun to drag him away. 

“What is it you want me to do?” Crowley stopped in his tracks. 

“Finish him. Finish him _your way_.” He turned to leave.

“Oh, good. My way.” Benny stopped and called after Crowley. “What is _‘my way’_?” Crowley rolled his eyes.

“Pick up one of those big rocks and hide behind that boulder. In a few minutes, the man in black will come running around the bend. The minute his head is in view, _hit it with the rock_!” he shouted, then stormed down the path and out of sight.

“My way’s not very sportsmanlike.” Benny reflected as he picked up one of the large rocks at his feet and crouched behind the boulder. 

True to Crowley’s predictions, the man in black rounded the bend within minutes. Benny tossed the rock, which shattered on the boulder next to the man’s head. Startled, the man drew his sword and turned to look at Benny, who laughed at how the man in black’s eyes widened at the sight of him. 

“I did that on purpose. I didn’t have to miss,” Benny hefted another rock into his hands. 

“I believe you,” the man looked cautiously from Benny to the large rock in his hands. “So, what happens now?” 

“We face each other as God intended,” Benny smiled. “Sportsmanlike. No tricks, no weapons. Just skill against skill.” 

“You mean that you’ll put down your rock and I’ll put down my sword and we’ll try to kill each other like civilized people?” the man asked. 

“I could kill you now if I wanted to,” Benny raised the rock over his head. The man slowly moved to put down his sword on the grass beside him.

“Frankly, I think the odds are slightly in your favor at hand to hand combat.” Benny did smile at this, a full blown, ear-to-ear grin.

“It isn’t my fault that I’m the biggest and the strongest,” he tossed the rock aside like a child’s toy. The man in black ran at Benny and slammed the full weight of his body into the giant, who barely even budged. The man in black backed up and tried again. This time he wrapped his arms around the giant’s waist to try and topple him. He grunted and Benny did his best not to laugh before the man in black finally released him and stepped back.

“Look, are you just messing around with me or what?” the man in black asked impatiently. 

“I just want you to feel like you’re doing well. I hate for people to die embarrassed.” Benny lunged at the man in black, but he rolled between his legs before he could be caught. “You’re pretty fast,”

“It’s a good thing that I am,” the man retorted. 

“Why are you wearing that mask?” Benny inquired. “Were you burned by acid or something?” He swung a fist at the man, who ducked.

“Oh, not at all. They happen to be terribly comfortable.” The man in black dodged another blow aimed at his head. “I think everyone will be wearing them pretty soon.” He dodged a third punch, ducked under Benny’s arm and leapt up onto a nearby rock, which he used to vault onto Benny’s back and wrap his arms tightly around the giant’s neck. 

“I just figured out why you give me so much trouble.” Benny tried to dislodge the man from his back, with no luck. He backed into a large boulder and slammed the man in black into it. 

“And why is that?” the man panted. Benny struggled to pull himself forward when black spots started to dance across his vision. 

“Well, I haven’t fought just one person in a very long time,” he grunted as he tried to shift the man’s arms off of his windpipe, to no avail. “I’ve been specializing in groups. Battling in gangs for local charities, that sort of thing.” He forced the man against another boulder. 

“Why should that make such a—“he groaned as his back slammed against the boulder.“—difference?” Benny’s breaths came in shorter and shorter as the man’s arms tightened around his neck and he slowly sunk to his knees.

“Well, you see…you use different moves…when you’re fighting…half a dozen people…than when you only…have to be worried…about one.” Benny collapsed. The man in black sprawled on top of him and gasped for breath. 

The man in black eased himself off of the unconscious giant, rolled his body over and pressed an ear to his chest. When he was sure that the giant’s heart was still beating, he pushed himself up to look Benny in the face. 

“I’m not jealous of the headache you’ll have when you wake up, but in the meantime, rest well and dream of large women,” he told the unconscious man, then retrieved his sword from where it lay, untouched, in the grass and raced ahead in pursuit of Crowley.

\---OoO---  
As soon as the horse bearing the army uniform of Guilder reached the castle, the guards alerted Prince Michael, who gathered a party of soldiers along with himself and Lucifer to search for his betrothed. Simply by sheer luck, the party docked at the port nearest to the Cliffs of Insanity, and had reached the top within the hour. Prince Michael dismounted his horse and crouched low to the ground before he stood back up and moved into his en gardé. He advanced and retreated without a partner across the battlefield, then abruptly stopped and turned to face the search party. 

“There was a mighty duel here. It spanned the entire area. They must have both been masters,” he announced while he continued to follow the footsteps in the dust until he reached the party. 

“Who won?” Lucifer spoke up from his horse. “How did it end?” 

“The loser ran off alone,” Michael pointed to the footsteps leading back where they had come from, then followed the other steps which lead to through the archway and up the path. “But the winner followed those footprints towards Guilder.” He pointed to the last, faintest set of footprints, two average and one belonging to someone colossal. 

“Should we track them both?” Lucifer asked. Michael shook his head.

“The loser means nothing to me. Only the Prince matters.” He moved to stand in front of the search party and raised his voice to address all of them. “Clearly, this was all planned by warriors of Guilder! We need to be ready for whatever might lie ahead.” Michael mounted his horse.

“Could this be a trap?” Lucifer inquired just loud enough for some of the other soldiers to hear.

“I think everything is a trap,” Michael smirked at Lucifer. “Which is why I’m still alive.” He spurred on his horse to follow the tracks headed towards Guilder.


	7. The Battle of Wits

**Summary for the Chapter:**

> “Let me put it this way: have you ever heard of Plato? Aristotle? Socrates?” The man in black nodded. “Morons, the lot of them.” 
> 
> “Really? In that case, I challenge you to a battle of wits.”
> 
> “For the Prince?” The man raised an eyebrow. “To the death?” His smile widened. “I accept.”

Crowley forced Dean up to the top of the hill where a small meal had been set out on a tablecloth placed on a rock and shoved him to the ground before he grabbed a strip of white linen out of the pouch at his side and tied it around Dean’s eyes. He then dragged Dean to a small rise in the ground in front of the rock and pushed him into a sitting position. Dean glared at Crowley from under his blindfold, but he ignored him. He sat down beside Dean and drew a dagger from his belt. He waited patiently next to Dean until he saw the man in black run up the hill, then he placed the tip of the dagger at Dean’s throat. The man stopped in his tracks when he saw the dagger glinting in the sun. 

“So, it seems that I am the last man standing, as it were.” Crowley sneered. The man slowly began to advance on Crowley. “If you want him dead, then by all means, keep moving forward.” The man halted and spread his arms in surrender.

“Let me explain—“

“There’s nothing to explain.” Crowley retorted. “You’re trying to kidnap what I’ve already stolen.” 

“Perhaps…we could make an arrangement?” The man took a cautious step forward. Crowley hauled Dean closer and pressed the blade more firmly against his throat. 

“There will be no arrangement, and you’re killing him.” He moved the blade a hair closer and just barely nicked the skin of Dean’s neck. Dean sucked in a startled breath and the man in black took a step back. 

“If there can be no arrangement, then we are at an impasse.” He spread his arms wide with a cocky smile on his face. 

“I’m afraid we are.” Crowley didn’t move the dagger. “I can’t compete with you physically, and you’re no match for my intelligence.” 

“You’re that smart?”

“Let me put it this way: have you ever heard of Plato? Aristotle? Socrates?” The man in black nodded. “Morons, the lot of them.” 

“Really? In that case, I challenge you to a battle of wits.”

“For the Prince?” The man raised an eyebrow. “To the death?” His smile widened. “I accept.” Crowley finally sheathed his dagger and Dean relaxed.

“Good. Pour the wine.” The man ordered as he seated himself across from Crowley. He did as he was asked, and poured while the man in black removed a small pipe from his pocket and extended it to Crowley. “Inhale this, but do not touch it.” Crowley did as he was commanded but never let his air of confidence waver while he did so.

“I don’t smell anything.”

“What you do not smell is called Iocane powder. It’s odorless, tasteless, dissolves instantly in liquid, and is one of the most deadly poisons known to man.” The man in black told him. Crowley’s cocksure smirk didn’t falter even for an instant as the man took both of the goblets as well as the pipe of Iocane and turned his back. The goblets clinked as the man in black worked, then turned back, exchanged the placement of the goblets several times, and finally set them back on the rock, one in front of himself and one in front of Crowley. “Now, where is the poison? The battle of wits has begun. It ends when you decide and we both drink and find out who is right…and who is dead.” 

“But it’s so simple! All I have to do is make an educated guess from what I know of you. Are you the sort of man who would put the poison into his own goblet or his enemy’s? Now, a _clever_ man would put the poison into his own goblet, because he knows that only a great fool would reach for what he’s given. I, however, am not a great fool, so I can clearly not choose the wine in front of you. But you must have known I was not a great fool. You would have counted on it! So, I can clearly not choose the wine in front of me.” 

“You’ve made your decision, then?” Crowley laughed.

“Not even close! Because Iocane comes from Australia, as everyone knows, and Australia is entirely populated by criminals, and criminals are used to having people not trust them, as _you_ are not trusted by _me_ , so I can clearly not choose the wine in front of you!”

“Truly, you have a staggering intellect.”

“Wait until I get going!” Crowley paused and squinted at the sky. “Where was I?”

“Australia.”

“Ah, yes! Australia. You must have suspected that I would know the powder’s origin, so I can clearly not choose the wine in front of me.”

“Now you’re just stalling.” 

“You like to think that, wouldn’t you‽ You’ve beaten my giant, which means you’re alarmingly strong, so you could have put the poison into your own goblet, and trust your strength to save you, so I can clearly not choose the wine in front of you! But you’ve also beaten my swordsman, which means you must have studied, and in studying you must have learned that man is mortal, so you would have put the poison as far away from yourself as possible, so I can clearly not choose the wine in front of me!”

“You’re trying to trick me into giving something away.” The man in black said. “It won’t work.” 

“It _has_ worked! You’ve given _everything_ away, I know where the poison is!”

“Then make your choice.” He challenged. 

“I will! And I choose—what in the world could that be?” Crowley pointed at something in the distance over the man in black’s shoulder and he turned his back to look.

“What? Where?” While the man in black was occupied, Crowley switched the placement of the two goblets on the rock so that the man in black’s goblet was where his own had been and vice versa. He turned back just as Crowley finished. “I don’t see anything.” 

“I could have sworn I saw something…never mind.” Crowley chortled. The man tilted his head to the side.

“What’s so funny?” 

“I’ll tell you in a minute. First, let’s drink! Me, from my glass, and you, from yours.” Crowley raised his goblet in a mock toast, watched as the man did the same and waited until the man in black took a drink before he raised his own goblet to his lips and drained the whole thing. The man in black smiled as they put their goblets down.

“You’ve guessed wrong.” He announced triumphantly. 

“You only _think_ that I’ve guessed wrong, that’s what’s so funny! I switched our glasses when your back was turned, you dunce!” Crowley mocked. “You’ve fallen victim to one of the classic blunders! The most famous is ‘never get involved in a land war in Asia.’ But second, only slightly less well known is this: ‘never go up against an Englishman when death is on the line!” Crowley threw back his head and laughed for several seconds before he stopped abruptly and fell to the ground. 

Dean strained what to see what had happened from beneath his blindfold when he felt hands touch his face. Instinctively, he flinched away, but they only stayed long enough to remove his blindfold. The first thing Dean noticed was the man’s eyes. Piercing blue the likes of which he hadn’t seen since…

“Who are you?” The man in black looked away and Dean felt bereft to no longer have those eyes on him. 

“Not someone to be trifled with. That’s all you’ll ever need to know.” Dean looked beside him and saw Crowley on the grass, still as a stone, eyes still open, frozen mid-laugh. It dawned on Dean exactly what had happened.

“So then, the poison was in your goblet the whole time.” 

“Actually, they were both poisoned.” The man in black looked pleased with himself as he helped Dean to his feet. “I spent the last few years building up an immunity to Iocane powder.” He admitted as he led Dean away.

\---OoO---

Prince Michael and the search party arrived at a hilly area littered with large rocks and boulders. Michael noticed the trampled grass, and the footsteps of the colossus’s feet along with those of the man from before.

“Someone has beaten a giant.” He proclaimed, as he stood. “There will be great suffering in Guilder if he dies.” He leapt back onto his horse and spurred the part onward, following the smaller man’s footsteps further up the hill.


	8. The Dread Pirate Roberts

**Summary for the Chapter:**

> “On the high seas, your ship attacked. The Dread Pirate Roberts never takes prisoners.” Dean accused.
> 
> “I can’t afford to make exceptions!” He leaned back on his hands casually. “I mean, once people hear that a pirate has gone soft, people will begin to challenge him, and then it’s nothing but work, work, work all the time!”
> 
> “Don’t mock my pain!” Dean shouted.
> 
> “Life is pain, Highness!” He fired back. “Anyone who says differently is selling something.”

The man in black pulled Dean across the vast expanse of grasses and exposed rocks atop the tall hill. He checked behind them every so often to ensure that they were not being followed. His grip on Dean’s wrist was firm, but not cruel like Crowley’s had been. He tossed Dean to the side, who stumbled and caught himself against a rock.

“Catch your breath.” The man in black ordered while he searched the horizon for any sign of followers. 

“What are you after? Money? Power? If you take me back, I can make sure you get anything you want.” Dean bargained. The man laughed and leaned against a large boulder.

“What’s that supposed to be worth? The promise of a _nobleman_. You’re very funny, Highness.” Dean narrowed his eyes.

“I was trying to give you a chance. It doesn’t matter where you take me. Prince Michael is the best hunter in the kingdom. He could track a falcon on a cloudy day, and he _will_ find you.” Dean told the man.

“You think your dearest love will save you?” The man raised an eyebrow at Dean. 

“I never said he was my dearest love!” Dean retorted. “And yes, he will.” 

“You’ve just admitted that you don’t love your fiancé.” The man advanced on Dean.

“He knows I don’t.” 

“You mean you’re not capable of love.” The man sneered. Dean stood to look the man in the eyes.

“I’ve loved more deeply than a _killer_ like you could ever dream!” The man raised his hand as if to slap Dean, but stopped himself. When he spoke again, there was ice in his voice.

“That was a warning, Highness. The next time my hand flies on its own. Where I come from, there are penalties when a man lies.” He grabbed Dean’s hand and yanked him forward as they continued on.

\---OoO---

Prince Michael and the search party crested the hill and came upon Crowley’s body, untouched, a small pipe lying on the rock beside a half-drunken goblet of wine. Michael carefully sniffed at the contents, then set the pipe back down.

“Iocane. I’d bed my life on it.” He pointed at the two sets of footprints leading up the slope. “There are the Prince’s footprints! He’s alive, or he was an hour ago. If he isn’t when I find him, I will be very annoyed.” He jumped on his horse and spurred the party forward.

\---OoO---

The man in black lead Dean to an area blocked from view on one side by boulders, and a steep slope down into a ravine on the other. He shoved Dean down onto a rock and turned his back.

“Take a break, Highness.”

“I know who you are!” The man in black’s shoulders went rigid as he turned to face Dean. “I knew it from the start. Admit it, you’re the Dread Pirate Roberts.” The man visibly relaxed and he smiled.

“With pride.” He gave a mock bow. “What can I do for you?”

“You can die a slow and painful death.” Dean bit out. Roberts tutted at him.

“Hardly complimentary, your Highness. Why do you feel the need to throw your venom at me?” He smirked.

“You killed my love.” Roberts stopped to think.

“It’s possible.” He shrugged. “I kill a lot of people.” Dean looked away and Roberts approached him. “Who was this ‘love’ of yours? Another ugly, rich, stuffy prince?” He asked as he lowered himself onto a rock across from Dean.

“No!” Dean spat. “A farm boy. He was poor. Poor and perfect. With eyes like the sea after a storm…” Dean trailed off as he lost himself in his memories. Roberts hummed and Dean snapped out of it. “On the high seas, your ship attacked. The Dread Pirate Roberts never takes prisoners.” Dean accused.

“I can’t afford to make exceptions!” He leaned back on his hands casually. “I mean, once people hear that a pirate has gone soft, people will begin to challenge him, and then it’s nothing but work, work, work all the time!”

“Don’t mock my pain!” Dean shouted.

“Life _is_ pain, Highness!” He fired back. “Anyone who says differently is selling something.” Dean turned his head away and Roberts huffed out a sigh as he got to his feet. “I think I remember this farm boy of yours.” A spark of hope entered Dean’s eyes. “This would have been…what, five years ago?” He noticed the tears in Dean’s eyes. “Does it bother you to hear this?” 

“There isn’t anything you can say that would upset me.”

“He died an honorable death. That should make you happy.” Roberts assured him as he moved stare over the slope. “No attempts at bribery or blubbering. He only said, ‘Please. Please, I need to live.’ It was the please that caught my attention.” Roberts turned back to face Dean. “I asked what was so important to him. ‘True love.’ He replied.” Dean looked up at Roberts, who smirked at him. “And then, he spoke of a man of surpassing beauty and faithfulness. I can only assume he meant you.” Roberts mocked. “You should thank me for destroying him before he found out what you really are.”

“And what am I?” Dean stood to stare Roberts in the face.

“Faithfulness. He talked about your enduring _faithfulness_. Now be honest with me, when you found out he was gone, did you betroth yourself to your prince in the same hour or did you wait a week out of respect for the dead?” Roberts fumed. 

“You’ve already mocked me once, never do it again!” Dean shouted. “I died that day!” Hoof beats sounded in the distance and Roberts looked towards the source. Dean seized the opportunity to take what little revenge he could. ”You can die too, for all I care!” Dean shoved the man firmly and sent him rolling down the slope into the ravine. 

“As you wish!” Roberts shouted as he rolled down the hill. Dean’s eyes widened in shock.

“Cas?” He breathed in disbelief. “Cas‽ Oh my God, what did I just do?” Dean threw himself down the hill and tumbled after Castiel. They both swore colorfully as they knocked into bumps and rocks on the way down.

“They’ve disappeared!” One of Michael’s soldiers told him as he scanned the area for any sign of the two men. “They must have seen us closing in, which might have accounted for his panicking.” 

“Unless I’m wrong,” Michael told the soldier. “And I am _never_ wrong, they’re heading straight into the fire swamp.” He spurred the search party onward without noticing Dean and Castiel at the bottom of the ravine.

Castiel pulled his mask and head scarf the rest of the way off and carefully made his way over to Dean, who was still sprawled out on the ground. At first, Castiel thought that he was breathing heavily from his fall down the hill, but then he realized that Dean was crying. He wrapped one arm around Dean’s waist and the other hand came up to cradle his head.

“Can you move?” He asked. Dean’s smile lit up the ravine even through his tears.

“Move? You’re _alive_. If you want, I could fly.” Dean pulled Castiel into a fierce hug and took in the familiar scent of him, the feel of Castiel’s arms around him. Dean cried into Castiel’s hair as his hands tightened their grip on Castiel’s back, which he noticed was shaking slightly, and Dean knew that he wasn’t the only one affected by their reunion. Castiel drew back to look in Dean’s eyes with his face cradled in one hand and stroked his thumb gently over Dean’s cheekbone.

“I told you I would always come for you. Why didn’t you wait for me?” Castiel asked.

“You were dead.” Even with Castiel inches away from him it still hurt to say. Castiel smiled at him and Dean returned it with one of his own.

“Death cannot stop true love. All it can do is delay it for a little while.”

“I’ll never doubt you again.” Dean promised.

“You won’t ever need to.” Castiel dragged Dean up for a kiss. Dean sighed contentedly and pulled him closer as his tongue ran across Castiel’s lips. Castiel gladly let him in and circled his hand to the back of Dean’s neck to support him. Castiel broke the kiss to place light, airy kisses all over Dean’s face, his nose, his cheeks, his eyelids, then trailed his lips down Dean’s jawline to his pulse, where he sucked a mark into the skin there.

They broke apart at the sound of horses up above them. Castiel got up and helped Dean to his feet, keeping hold of his hand and he pulled Dean behind him once more, this time as a willing companion. They were mere feet away from the entrance to the Fire Swamp when they were spotted by Michael’s soldiers. Castiel merely laughed.

“Your pig of a fiancé is too late! A few more steps and we’ll be safe in the Fire Swamp.” He continued but now Dean trailed behind him reluctantly. 

“We’ll never survive in there!” He hissed.

“Nonsense!” Castiel didn’t even stop. “You’re only saying that because no one ever has.”


	9. The Fire Swamp

**Summary for the Chapter:**

> “I mean, what are the three terrors of the Fire Swamp?” He grabbed his sword and began to inch Dean away from the rodents. “First, the flame spurts. No problem! There’s a popping sound preceding each, so that’s easily avoided. Second, the lightning sand. You were clever enough to find out what that looks like, so in the future we can avoid that too!” Dean stopped them.
> 
> “What about the ROUS-es?” Dean asked and Castiel laughed.
> 
> “The Rodents of Unusual Size? I don’t think they even exist.” He assured him, then was tackled to the ground.

Castiel led Dean through the thick foliage that marked the entrance to the Fire Swamp. When their eyes had adjusted to the dim light, Dean looked at their surroundings. The Fire Swamp seemed to be made almost entirely of thick vines and trees so tall that he could hardly see the branches. As they ventured further into the Fire Swamp, something growled menacingly behind Dean, followed by a piercing shriek that caused him to flinch. Castiel wrapped his arm around Dean’s waist and tugged him closer to his side.

“It’s not _that_ bad, really.” Dean gave him an incredulous look. “I’m not saying I’d like to build a summer house here, but the trees really are beautiful.” In the distance something creaked and a massive boom echoed around them. Dean raised an eyebrow and Castiel shrugged. 

As the path narrowed, Castiel shifted his grip around Dean’s waist to hold his hand and put himself in front of Dean. They passed under a raised tree root that had grown out of the ground and Dean startled at a loud popping noise to his right. Castiel looked around for its source, but continued when he found nothing. Seconds later, a burst of flame shot out of the ground and set the leg of Dean’s trousers on fire. 

Dean screamed, then found himself sitting against a tree trunk while Castiel knelt in front of him and efficiently worked to put out the fire. When it was completely extinguished, Dean sighed. Castiel cupped his cheek. 

“Now that was an adventure!” Castiel helped Dean to his feet. “Get a bit singed there?” Castiel brushed an errant piece of hair out of Dean’s eyes, and he smiled.

“Not really. You?” Castiel shook his head and took Dean’s hand. The loud popping noise sounded again to Dean’s left, and this time Castiel lifted him out of the way just as the flame burst out of the soil.

 

“I’ll say this much: the Fire Swamp definitely keeps you on your toes.” He remarked as he pulled Dean behind him. The path gently sloped upward and the vines slowly drooped lower and lower, until the only way through was for Castiel to cut them down. “Soon, this will all be just a happy memory!” He hacked away a section of vines. “Because Roberts’ ship, _Revenge_ , is anchored at the far end. And I, as you know, am Roberts.”

“How is that possible? He’s been marauding for over twenty years and you only left me five years ago.” Dean asked as Castiel cut a large swath in the vines. 

“I myself am often surprised at life’s little quirks.” He stabbed his sword into the ground just in time to lift Dean away from another sudden burst of flames. “See, what I told you before about saying please was true. It intrigued Roberts, as did my description of your beauty.” Dean shoved him. “Finally, Roberts decided something. He said, ‘All right, Castiel. I’ve never had a valet. You can try it for tonight. I’ll most likely kill you in the morning.’” Castiel hacked down a particularly large vine. “He told me that for three years! ‘Good night, Castiel. Good work. Sleep well. I’ll most likely kill you in the morning.’ It was a good time for me. I learned how to fence, fight, I learned anything people would teach me. Eventually, Roberts and I became friends, and then, it happened.” He stopped.

“What?” Dean asked. Castiel shook his head and continued forward. “Go on!” Castiel sighed dramatically.

“Well, Roberts had grown so rich that he wanted to retire, so he took me to his cabin and told me a secret. ‘I am not the Dread Pirate Roberts.’ He said.” Castiel lifted Dean into his arms and carried him over a large tree root, then decided to keep carrying him rather than put him down, much to Dean’s chagrin. “’My name is Ryan!’ He said. ‘I inherited this ship from the previous Dread Pirate Roberts, just as you will inherit it from me. The man I inherited it from was not the Dread Pirate Roberts either! His name was Cummerbund. The _real_ Roberts has been retired for fifteen years, living like a king in Patagonia.’” Dean looked at him in amazement. 

“Then he explained that the name was the important thing for inspiring the necessary fear. You see, no one would surrender to the Dread Pirate Castiel.” He finally set Dean back on his feet. “So, we sailed ashore, took on an entirely new crew, and he stayed aboard for a while as my first mate, all the while calling me ‘Roberts.’ Once the crew believed, he left the ship, and I’ve been Roberts ever since. But, now that I’ve found you, I’m going to retire and hand the name over to someone else.” He leaned in to press a chaste kiss to Dean’s lips. “Do you understand now?” Dean nodded, took a step forward, and vanished into a sand pit. 

Castiel hurriedly hacked a vine in half, grabbed on to one end and dove in after Dean. He fell in as far as the vine allowed, then felt around with his other arm. His hand brushed against what felt like a shirtsleeve over a flailing arm. He grabbed it and tugged it towards him, certain that it was Dean when the arm wrapped itself around him and clung to Castiel like a lifeline. Slowly, Castiel began to pull them out. 

They both gasped for breath as they finally broke the surface of the sand. Castiel and Dean were both covered in sand and their chests heaved as they lay sprawled out on their backs, inches away from the pit. Castiel took a few moments to catch his breath before he crawled over to Dean and helped him prop himself up against a raised tree root. 

As soon as Dean was upright he pulled Castiel into a fierce hug while Castiel rubbed calming circles on Dean’s back and whispered reassurances in his ear until he had calmed down. The two men remained that way for several minutes until Castiel looked up and saw two unusually sized rodents staring at them. 

“We’ll never make it out of here alive.” Dean shook in Castiel’s arms and he pulled back to look Dean in the eyes.

“No! I promise, we will make it out alive.” He shakily rose to his feet and supported Dean until he was steady enough to stand. “I mean, what are the three terrors of the Fire Swamp?” He grabbed his sword and began to inch Dean away from the rodents. “First, the flame spurts. No problem! There’s a popping sound preceding each, so that’s easily avoided. Second, the lightning sand. You were clever enough to find out what that looks like, so in the future we can avoid that too!” Dean stopped them.

“What about the ROUS-es?” Dean asked and Castiel laughed.

“The Rodents of Unusual Size? I don’t think they even exist.” He assured him, then was tackled to the ground. The ROUS pinned him firmly to the damp earth with its massive body. Dean leaped back, startled, and then tried to find something he could use to hit it with. The ROUS snarled at Castiel, who raised his arm in defense, only to have to rodent clamp it jaws around his forearm. Castiel cried out in pain.

“Cas!” Dean yelled, before he noticed Castiel’s sword, which had been knocked aside when the rodent tackled him. He slowly inched his way around the pair, careful not to draw the thing’s attention, when Castiel landed a solid punch to its jaw, and it rolled off to one side. Dean was frozen as he watched Castiel try to grab his sword, but the ROUS pulled him just out of reach and snapped at his face. 

Castiel grabbed the thing by the teeth and rolled the ROUS over, himself with it. The two rolled back and forth until the rodent landed on top of Castiel again and sank its blunt teeth into the meat of his shoulder. Castiel screamed, then heard a popping noise a few feet to his left. He rolled the both of them towards it, then shoved the rodent into the burst of flame as it spouted out of the ground. He turned to grab his sword from where it had fallen, but it was nowhere to be seen. The rodent howled in pain behind him and he whirled around to see Dean looming over the ROUS with his sword driven into the ROUS’s heart. 

Dean waited until he was sure the thing was dead, then pulled Castiel’s sword out of its chest and looked up to see Castiel staring at him in awe. He wiped the blade off on the dead leaves littering the floor before he handed it back to Castiel. He sheathed it, then yanked Dean to him and crushed their mouths together in a bruising kiss. When they broke for air, Castiel pressed his forehead against Dean’s.

“Where did you learn to fight like that?” Dean grinned.

“You’re not the only one who learned anything he could. I’ll tell you the whole story later. Right now, I want to go somewhere it can just be the two of us.” Castiel smiled and brushed a soft kiss over Dean’s cheekbone.

As you wish.” Then Castiel had a revelation. “Dean. Do you remember telling me about your younger brother?” Dean stopped.

“Yeah, I do. Why?” Castiel hated to bring up a subject that clearly caused Dean a lot of pain, but he needed to make sure that Dean knew. 

“Sam is alive.” Dean’s jaw dropped.

“No, that…that can’t be right. Mom told me he died.” Castiel squeezed his hands.

“I know, but Dean, I saw him. He said his father’s name was John Winchester and that he was a sword maker.” Dean sucked in a breath through his teeth.

“Gods, it was really him. Where was he? What was he doing?” Castiel refused to meet Dean’s eyes. “Cas, tell me! It’s fine, I can take it.”

“He was working for Crowley.” 

“No.”

“Dean—“

“No! He—Sammy wouldn’t do that to me! He wouldn’t!” Castiel could see that tears had begun to gather in Dean’s eyes.

“He doesn’t know you’re his brother. He can’t.” Dean’s heart shattered. “If it helps at all, he said that he was only working for Crowley to survive while he hunts down the man that killed your father.” Castiel would be lying if he said that he was surprised to see that this seemed to perk Dean up. “What did your mother tell you about Sam’s death?”

“Not much. She said she never got much of the story out of Dad, only that they’d been out hunting, and Sammy had been killed by a wild animal. He left a few days after that and we never heard from him again. Cas, do you…do you think my dad lied to my mom about Sam?” 

“I think so. I can’t imagine why he would, but I doubt it was anything good.” Dean nodded.

“So, that tall guy with the shaggy hair…that was Sammy? He can’t have been the giant, he was always such a tiny kid.” Castiel nodded.

“You’d be proud of him, Dean. He’s a brilliant fencer.” Dean’s face paled.

“What happened to him?” Castiel tilted his head before he realized why Dean had asked him. His eyes widened and he scrambled to answer.

“He’s fine! I beat him in a duel and he begged me to give him a quick death—“ Dean winced. “But I didn’t kill him! I knew I couldn’t afford to have anybody that worked for Crowley following me, even if he is your brother, so I knocked him out. He’ll probably have a bad knot on his head for a few days, but that’s all.” Dean visibly relaxed. 

“Have I told you how much I love you?” Castiel kissed him.

“Yes, but I find that you can never say it too many times.” Dean grinned.

“I love you.”

“I know.” Dean shoved him away as Castiel threw his head back and laughed.


	10. The Pit of Despair

**Summary for the Chapter:**

> He slowly opened his eyes and the face of a slimy looking older man came into focus directly above him.
> 
> “Where am I?” Castiel grated. His throat felt like a fire ant colony had taken up residence inside, and his tongue stuck to the roof of his mouth when he tried to speak.
> 
> “The Pit of Despair.” The man hissed ominously. “Don’t even—“He trailed off into a coughing fit, then sighed dramatically as he turned back to look at Castiel. “Don’t even think about trying to escape.” He told Castiel, now without the dramatic voice.

Dean nearly wept for joy when they finally reached the other end of the Fire Swamp. He winced at the sudden brightness, and Castiel laughed at the face he was making. Dean shoved him with his shoulder, and Castiel turned Dean to face him, then rested their foreheads together to shield Dean from the sun.

“Better?” He asked. Dean grinned and leaned in for a kiss, when they were suddenly interrupted by thundering hoof beats. They separated, and Castiel drew his sword while he wrapped an arm around Dean’s waist and tucked him safely against his side. The small formation of horses parted to make way for Lucifer and Prince Michael to come to the forefront. 

“Surrender!” Prince Michael commanded. 

“You’ve come to surrender to me?” Castiel smirked, and lowered his sword. “I accept.” Prince Michael gave a mirthless smile.

“I give you full marks for your bravery, but it doesn’t make you any less of a fool.” Castiel caught the hostility in Prince Michael’s tone, and shifted so that Dean was behind him.

“You’re going to capture us, then? How would you do that, exactly? We know the secrets of the Fire Swamp and can be quite content there for some time, so whenever you feel like dying, be sure to pay us a visit.” Dean surveyed the trees around them and saw archers quietly step into place, crossbows notched and aimed directly at Castiel.

“Surrender! I will not ask you again.” Prince Michael warned, and Dean saw him twitch his left hand at Lucifer, who sneered. 

“That will never happen.” Castiel insisted. Dean could tell that Michael was becoming impatient.

“For the last time, _surrender_!” Michael commanded.

“Death first!” Castiel yelled, sword raised. Dean saw Lucifer lift his hand in preparation to signal the archers. He rushed forward to stand in front of Castiel.

“Promise me you won’t hurt him!”

“What was that?” Castiel and Michael asked simultaneously.

“If we surrender and I come back with you,” Dean took a step towards Michael. “Will you promise not to hurt this man?” Michael looked at Dean in shock, but gave a slight nod.

“May I live a thousand years and never hunt again.” He vowed, and Dean shot Castiel an apologetic look before he continued. 

“This is the Dread Pirate Roberts. He’s a sailor on the pirate ship _Revenge_. You will return him to his ship, unharmed.” Dean demanded. Again, Michael nodded his head in acquiescence.

“I swear it will be done.” He motioned for the archers to lower their crossbows and waited for Dean to look the other way before he beckoned Lucifer closer and leaned over to whisper in his ear. “As soon as Dean and I are out of sight, take him back to Florin and throw him in the Pit of Despair.” 

“I swear it will be done.” Lucifer responded in a mockery of Michael’s pledge. The two men shared a smile as they nudged their horses closer to the two lovers. Dean saw them approach and pulled Castiel into an embrace.

“I thought you were dead once and it almost killed me.” Dean pulled back to look into Castiel’s eyes. “I can’t stand to let you die again, not when I can save you.” He gave him a hopeful smile and cupped his cheek. Castiel closed his eyes tightly and clasped his hand over Dean’s. 

Michael pulled his horse to a stop in front of the two men, and Dean reluctantly pulled away to mount the horse, which Michael spurred forward the instant Dean was settled and left Castiel alone with Lucifer and the guards. Castiel watched them leave with his hands clenched into fists at his sides. As soon as they were out of sight, Lucifer broke Castiel out of his reverie. 

“Come, sir.” He spoke drily. “We must return you to your ship.” Castiel rolled his eyes.

“We are men of action.” Castiel sauntered forward to stand in front of Lucifer’s horse. “Lies don’t suit us.” Lucifer’s lips twisted upwards into an unnerving parody of a smile that made Castiel’s insides twist into knots. 

“Well said.” Lucifer waved his right hand at one of the guards, who began to bind Castiel’s hands behind his back. As he lifted his hand, Castiel noticed something peculiar. He tilted his head to the side which drew Lucifer’s attention. “What is it?”

“You have six fingers on your right hand.” Lucifer’s smile disappeared and he drew his sword. “Someone is looking for you.” Castiel’s comment was the last thing he was aware of before a burst of pain across the crown of his head, followed by enveloping darkness.

\---OoO---  
The first thing Castiel noticed when he regained consciousness was that he was restrained on some sort of table and that he was strapped down at his ankles and wrists. The next thing he noticed was the feeling of a cloth dabbing the wound on his shoulder. He slowly opened his eyes and the face of a slimy looking older man came into focus directly above him.

“Where am I?” Castiel grated. His throat felt like a fire ant colony had taken up residence inside, and his tongue stuck to the roof of his mouth when he tried to speak.

“The Pit of Despair.” The man hissed ominously. “Don’t even—“He trailed off into a coughing fit, then sighed dramatically as he turned back to look at Castiel. “Don’t even think about trying to escape.” He told Castiel, now without the dramatic voice. “These are the thickest chains in the land. Don’t bother getting your hopes up about being rescued either. The only way in our out is a secret.” He informed Castiel while he continued to dress his wound. “Only the Prince, Lucifer, and I know the way.”

“So I’m here until I die?” Castiel asked.

“Until they kill you. So, to answer your question, yes!” A manic smile appeared on the man’s face as he dabbed at Castiel’s wound. He winced as the man pressed down on a particularly sore spot.

“Then why waste your time curing me?” He questioned. The man’s smile grew wider and a cruel gleam lit up his cold eyes.

“The Prince and Lucifer prefer to have all of their guests healthy before they’re…broken.” 

“They’re going to torture me.” Castiel observed gravely. The man nodded excitedly. “I can handle torture.” The man laughed, and the sound chilled Castiel to the bone. “You don’t believe me?”

“You survived the Fire Swamp, so you have to be extremely brave, but _nobody_ can withstand The Machine.” He told Castiel, then turned away and left Castiel alone with his thoughts.

\---OoO---  
Michael and Lucifer were discussing their plans for Castiel while they wandered through the halls of the castle. Michael noticed that if they happened to cross Dean’s path along the way, his betrothed wouldn’t even react. Michael put an arm in front of Lucifer to stop him, and both men watched Dean pass them by, head hung low, shoulders slumped, and feet dragging. Michael sighed.

“He’s been like this ever since we came back from the Fire Swamp. It’s my father’s declining health that’s upsetting him.” Lucifer raised an eyebrow.

“Of course, my lord.”


	11. Nightmares

**Summary for the Chapter:**

> “Your True Love still lives!” One gnarled finger jabbed out at him. “You marry another, while your True Love lives!” Now the woman turned to the terrified crowd. “His True Love saved him in the Fire Swamp, and he treated him like garbage.” She spat the word out and Dean felt it hit him square in the chest and send him staggering backward a few steps. “That’s what he is! The King of refuse. So bow down to him, if you like, bow to him! Bow to the King of slime! The King of filth! The King of putrescence!”

King Charles of Florin died that very night. The next morning, Dean and Prince Michael were married. After the ceremony, Dean greeted the citizens of Florin again, this time as their King. Michael once again stood on the balcony high above the crowd, still in his wedding finery, his crown sparkling in the midday sun. 

“My father’s final words were: ‘Love her as I loved her, and there will be joy.’” Michael’s regal voice boomed out over the crowd. “I now present to you, your King, my husband. King Dean.” He swept his arm over to the archway. Trumpets blared and people cheered as Dean slowly emerged into the sunlight. His silver coat caught and reflected the light in dazzling arrays of color. As he passed by the assembled crowd, they all dropped to their knees and bowed. He reached the end of the path, ready to ascend the stairs to join Michael on the balcony, when a noise from behind him caught his attention.

“Boo!” A voice shouted from the crowd. “Boo!” The crowd parted as a horrific looking beggar woman rose to her feet.

“Why are you doing this?” Her face twisted into a hideous sneer.

“Because you had love in your hands!” She retorted and Dean recoiled. “You were in love, and you gave it up!” 

“They would have killed Cas if I hadn’t agreed to this!” Dean insisted.

“Your True Love still lives!” One gnarled finger jabbed out at him. “You marry another, while your True Love lives!” Now the woman turned to the terrified crowd. “His True Love _saved_ him in the Fire Swamp, and he treated him like _garbage_.” She spat the word out and Dean felt it hit him square in the chest and send him staggering backward a few steps. “That’s what he is! The King of _refuse_. So bow down to him, if you like, bow to him! Bow to the King of slime! The King of filth! The King of _putrescence_!” The woman turned back to face Dean, eyes ablaze. 

“Boo, boo!” Dean tried to back away from her as she approached him while she continued to hurl insults and obscenities. He turned to run, but never seemed to get any closer to the archway. The path stretched on and on in front of him for miles. He looked back to find her directly behind him, and he tried to get away, but she grabbed his ankle and yanked. He fell to the ground and she dragged him towards her. 

“Rubbish! Filth! Slime! Muck!” Her clammy hands closed around his neck and the crowd around him did nothing to stop her as she squeezed the life out of him while curses spewed from her mouth.

“CAS!” Dean sat bolt upright in bed, drenched in sweat as he recovered from the nightmare. He pressed his hands against his eyes and took in several deep breaths to compose himself. He took stock of where he was, and of what day it was now. The wedding was ten days away. As far as Dean was aware, the King was still alive. There was still time for Castiel to come and rescue him from this nightmare. The nightmares had begun a few days ago and had gotten steadily worse as the wedding approached. 

Before Dean realized what he was doing, he got out of his bed and raced down the hall to Michael’s chambers. He didn’t bother to knock, burst through the doors into Michael’s study, where the man sat at a large desk reading a book. He looked up at Dean as he came in, marked his place and set the book down.

“Here’s the deal.” Dean said, matter of fact. “I love Cas. Nothing will ever change that. If you say that I have to marry you in ten days, believe me when I tell you that I will be dead tomorrow morning.” His tone was low and deadly, and brokered no argument. Michael raised an eyebrow at Dean, then lowered it as he sighed and rubbed at his temples. 

“You know I could never cause you grief, Dean.” Michael replied.” Consider the wedding off, then.” Dean felt a weight lift off of his chest, and he felt like he could finally breathe. Michael looked over at Lucifer, who Dean only just noticed standing by the fire. “You returned this…Castiel…to his ship?”

“Yes.” Lucifer deadpanned.

“Then we must alert him.” Michael announced. “But I have to ask you this, Dean. Are you sure that he still wants you? You were the one who left him at the Fire Swamp, after all.” Michael reminded him. “Not to mention that pirates aren’t renowned for their honesty.”

“Cas will always come for me.” Dean had never been more certain of anything in his life. Michael mulled this over for a few moments, then brightened.

“How about this? You write four copies of a letter. I will send my four fastest ships, one in each direction. The Dread Pirate Roberts is always close to Florin this time of year. We’ll run up the white flag, and deliver your letter. If Castiel still wants you, then God bless you both. If not, please consider me as an alternative to suicide?” Michael gave Dean his most disarming smile, but now it just unnerved him. “Do we have a deal?” 

“We do.” Dean abruptly turned on his heel and stalked out of the room.

\---OoO---

“Your Prince is quite the fascinating creature.” Lucifer remarked as they made their way through the forest to the Pit. “A bit simple, perhaps, but his appeal is undeniable.” 

“I know. The people are quite fond of him.” Michael chuckled. “It’s strange. When I hired Crowley to have him murdered on our engagement day, I thought that was clever. But I think it will be so much more moving when I strangle him on our wedding night. Once we blame Guilder, the nation will be outraged. They’ll demand that we go to war.” He and Lucifer shared a laugh as they reached the entrance to the Pit.

“Now, where is that secret knot?” Lucifer ran his hands over the surface of the tree. “It’s impossible to find.” He pressed firmly against one of the larger knots, which gave way and opened a door in the tree. He made his way down the first few steps, then turned back to Michael. “Are you coming down into the Pit? Now that Castiel has his strength back, I’m starting him on the Machine.”

“Lucifer, you know how much I love watching you work, but I’ve got my country’s five hundredth anniversary to plan, my wedding to arrange, my husband to murder, and Guilder to frame for it. I’m swamped.” Lucifer nodded sympathetically.

“Get some rest. If you haven’t got your health, you haven’t got anything.” He patted Michael on the shoulder, then descended the rest of the way into the Pit. As he reached the bottom of the stairs, he saw that Zachariah had finished strapping the attachments for the Machine onto Castiel. Zachariah wheeled the table over to the massive contraption and began to connect Castiel to the Machine.

“Beautiful, isn’t it?” Lucifer asked. “It took me half a lifetime to invent it. I’m sure by now you’ve discovered my deep interest in pain. I’m actually writing the definitive work on the subject, so I want you to be completely honest with me on how the Machine makes you feel. Since this is our first try, I’ll use the lowest setting.” He moved over to a large lever and pushed it upwards slightly.

Castiel barely had time to register the sound of rushing water before the most intense physical pain he had ever experienced tore through him. He cried out through the gag covering his mouth, and his body jolted and seized as the Machine sent shockwaves of agony coursing through his body. He wasn’t aware of how much time passed before Lucifer mercifully pushed the lever back to its original position. Castiel was left boneless on the table to regain his breath through the aftershocks.

“As you know, the concept of the suction pump is centuries old, and that’s really all this is. There is one difference: instead of sucking water, I’m sucking life. I’ve just sucked one year of your life away. One day, I might be able to go as high as five, but I’m honestly not sure what that would do to you, so let’s just start with what he have. Tell me, what did this do to you? And remember, this is for posterity, so please be honest. How do you feel?”

Castiel opened his mouth to speak, but all the emerged was a pained whimper interspersed with gasps and sobs. The convulsions had stopped, and he lay limp on the table. Lucifer hummed thoughtfully and opened a large leather journal on the desk nearby and scribbled down the results.

“Interesting.”


	12. The Brute Squad

**Summary for the Chapter:**

> “You don’t look so good.” Benny informed Sam, who scoffed even as his knees buckled beneath him and Benny had to set him back on his feet. “You don’t smell so good either.”
> 
> “Maybe not,” Sam grinned. “But I feel fine.” Benny nodded and released his grip on the back of Sam’s shirt. Sam took one step forward and promptly fell flat on his face.

Michael was sifting through papers in his study, finalizing plans for Florin’s anniversary celebration as well as Dean’s murder, when Adam Milligan, the Captain of the Guard knocked on the door.

“Ah, Adam!” The young man gave a small bow. Michael rolled his eyes at the formality and waved Adam closer. The soldier rushed over and knelt beside Michael’s chair. “As chief enforcer of all of Florin, I am trusting you with this secret.” Michael told him, eyes serious. “Killers from Guilder have infiltrated the Thieves’ Forest and plan to murder my husband on our wedding night.” Adam looked shocked.

“My spy network has heard nothing of the sort, Highness.” Michael opened his mouth to reply when Dean burst into the room with his typical abruptness.

“Have you heard from Cas?” Adam frowned at Dean’s informal manner of addressing their Prince, but Michael shook his head at him.

“It’s too soon, my angel. You must be patient.”

“He _will_ come for me.” Dean gave Michael a smug smile.

“Of course.” Michael acquiesced. Dean turned on his heel and left. As soon as he was out of earshot, Michael looked back at Adam, his features once again grave and solemn. “He cannot be murdered! On the day of our wedding, I want the Thieves’ Forest emptied and every inhabitant arrested.” Adam sighed.

“Many of the thieves will resist, Sire. My regular enforcers will be inadequate.”

“Form a brute squad, then!” Michael raged. Adam’s eyes widened in shock, and Michael took a deep breath in to calm himself. “I want the Thieves’ Forest empty before Dean and I are wed.”

“It won’t be easy, Highness.” Michael raised an eyebrow.

“Try ruling the world sometime.” He told the Captain of the Guard. Adam mulled this over for a few moments, then stood, bowed, and took his leave. 

\---OoO---

The day of the wedding arrived, and the Brute Squad had their hands full carrying out Prince Michael’s orders. Adam rode at the front of the caravan that held the prisoners they had already apprehended. He called the foremost cart to a halt when Gordon Walker, one of his strongest enforcers, jogged up to the cart.

“Is everyone out?” Adam asked.

“Almost.” Gordon grimaced. “There’s a swordsman giving us some trouble.” Adam shot him a look that bordered on deadly.

“Then you give him some trouble.” Gordon nodded in compliance, and Adam spurred the caravan forward. Gordon carefully made his way over to the swordsman, who had propped himself up against the door to a hut and refused to move. The man was half-drowned himself in brandy and raving nonsense.

“I’m waiting for you, Crowley!” Sam shouted. “You told me to go back to the beginning! So I did. This is where I am, and this is where I’ll stay. I won’t be moved!” He screamed the last part at the enforcers that tried to get near him. Gordon approached him.

“You there!” Gordon called out. The man laughed and took another swig from the bottle at his side.

“I won’t budge. Shove your “you there” when the sun doesn’t shine.” Sam told him blandly.

“The Prince gave orders.” Gordon informed him. Sam suddenly leapt up and gave a sloppy thrust at Gordon before he stumbled and fell.

“So did Crowley!” Sam said as he hit his knees. “’When a job goes wrong, go back to the beginning.’ This is where we got the job, so _this_ ,” He gestured to the forest around them, “Is the beginning, and I’m staying here until Crowley comes.” 

“You, big guy, come here!” Gordon called over to one of the remaining Brute Squad. He kept a safe distance from Sam and made sure to keep one eye on him as he rose to his feet.

“I am waiting for Crowley. I’m not moving until then.” Sam insisted.

“They’ll put you in the pen.” A deep voice intoned from behind him. Large hands fisted in his shirt, easily lifted him up and set him on his feet. Sam grabbed on to the hands, which released him and opened up for Sam to compare his hand to the much bigger one. Confused, Sam looked up at Benny.

“Hello.” Benny supported Sam’s weight easily with one hand.

“It’s you.” Sam shot Benny a drunken smile.

“True.” Benny knocked Gordon in the jaw without so much as a glance over his shoulder and sent him sprawling on the ground. “You don’t look so good.” Benny informed Sam, who scoffed even as his knees buckled beneath him and Benny had to set him back on his feet. “You don’t smell so good either.”

“Maybe not,” Sam grinned. “But I _feel_ fine.” Benny nodded and released his grip on the back of Sam’s shirt. Sam took one step forward and promptly fell flat on his face. Benny rolled his eyes, hefted the inebriated Sam over his shoulder and brought him into his house in the forest. While he nursed Sam back into health and sobriety, he told the swordsman about Crowley’s death and the existence of Lucifer, the six-fingered man. When he heard this news, Sam fainted into the bowl of stew Benny had been feeding him. 

“I think he took the news pretty well.” Benny commented to himself as he dragged Sam over to the barrels of steaming and freezing water he had prepared earlier, then proceeded to repeatedly dunk Sam’s head into both barrels alternatively until Sam was alert and sober once more.

“That’s enough!” Sam shook Benny off and pushed his soaked hair out of his eyes. “Where is this…Lucifer now so I can kill him?” Sam demanded. 

“He’s with the Prince in the castle.” Sam perked up. “ _But_ the castle gate is guarded by thirty men.” Sam groaned and kicked over one of the stools at the table.

“How many could you handle?” Sam asked. Benny thought it over for a moment.

“I don’t think I could deal with any more than ten.” Benny told him solemnly. 

“That leaves twenty for me.” He swore and kicked the stool again. “I could never defeat that many, even at my best.” He sank to the floor and rested his head against his knees. “We need Crowley to make a plan. I’ve never been good with strategy.”

“Crowley’s dead.” Sam shot him a sarcastic look, then sat bolt upright.

“No.” He breathed. “No, we don’t need Crowley at all! We need the man in black. Think about it!” Sam exclaimed in response to Benny’s incredulous stare. “He bested you in strength, he bested me with steel, and he had to have out-thought Crowley! A man who can do that can plan a castle onslaught in his sleep! Let’s go!” Sam was well and truly excited now and he practically skipped to the door of the house. 

“Where to?” Benny asked, fazed by Sam’s uncharacteristic demeanor. 

“To find the man in black!” 

“But you don’t know where he is!” Sam scoffed.

“That doesn’t matter! After twenty years, my father’s soul will finally be at peace. There will be blood tonight!” Sam proclaimed as he bounded out the door.


	13. Ultimate Suffering

**Summary for the Chapter:**

> “You never sent those ships.” Michael began to protest. “Don’t lie to me, it won’t do you any good.” Dean smiled. “It doesn’t matter anyway. Castiel will come for me, with or without my letter.” Michael tutted.
> 
> “You’re very naïve.” Dean’s eyes blazed.
> 
> “Yeah I am, I’m naïve enough to not have noticed that you’re a coward with a heart full of fear until now.” Michael grabbed the dagger off of the whetstone and shoved it into the sheath on his belt.
> 
> “I would not say such things if I were you.”

Adam entered Michael’s chambers to find him sharpening a dagger with the whetstone at his desk. He knelt a few feet from the desk. Michael rolled his eyes. “You may stand. What news do you have?” Adam rose to his feet.

“We’ve emptied the Thieves’ Forest, and thirty men guard the castle gate.” 

“Double it.”

“But my Lord—“Adam protested.

“My Prince must be safe on our wedding day, Captain Milligan!” Michael pointed the dagger in his face. “He’s been so withdrawn of late. I’m worried that someone might try to take him from me at our wedding.”

“The castle gate has only one key, Highness.” Adam raised a small pouch embroidered with the royal seal of Florin. “And I keep it with me at all times.” Michael placed the dagger down on the whetstone and rose to greet Dean as the young man rushed into the room unannounced. 

“Hello, my darling.” Adam was smart enough not to comment on Dean’s flinch when Michael took his hands. “Tonight we shall be married. Tomorrow morning, Captain Milligan’s men will escort us to Florin channel where every ship in my armada waits to accompany us on our honeymoon.”

“Except for your four fastest.”

“What, my dearest?” Dean extricated his hands from Michael’s.

“Every ship but your four fastest.” Michael blinked at him. “The four that you sent after Castiel?”

“Yes, yes, of course, dearest. Naturally, those four won’t be there.” Michael shot Adam a look, and he cleared his throat.

“If you’ll excuse me your majesty.” Michael nodded and Dean didn’t bother to wait before he was out of earshot before he confronted Michael.

“You never sent those ships.” Michael began to protest. “Don’t lie to me, it won’t do you any good.” Dean smiled. “It doesn’t matter anyway. Castiel will come for me, with or without my letter.” Michael tutted.

“You’re very naïve.” Dean’s eyes blazed.

“Yeah I am, I’m naïve enough to not have noticed that you’re a coward with a heart full of fear until now.” Michael grabbed the dagger off of the whetstone and shoved it into the sheath on his belt.

“I would not say such things if I were you.”

“Why not? You can’t touch me! Cas and I love each other, and you’ll never be able to track it, not with a thousand bloodhounds. And you can’t break it either, not with a thousand swords. And when I say you’re a coward, I mean you’re the slimiest weakling that ever walked the earth!” Michael slammed his hands down on his desk, grabbed Dean’s arm and dragged him down the hall to his room in a fit of rage.

“I would not say such things if I were you!” Michael shoved him roughly into his room and bolted the door behind him from the outside. He called two guards over. “You there! Guard this room with your lives. My beloved is not to leave for any reason whatsoever. Understood?” The guards nodded and Michael raced from the castle, out a secret exit into the Thieves’ Forest and directly into the Pit of Despair where Lucifer was about to put Castiel through another trial on the Machine. He stalked forward, shoved Zachariah out of the way and loomed over Castiel’s face. 

“You and Dean clearly love each other very much, and you might have been truly happy together. I don’t care what the story books say, not a single couple in a century has had that chance.” Castiel tried to tilt his head despite the straps. “That’s why I think that no man in a century will suffer as greatly as you will.” Michael turned and thrust the Machine lever to its highest setting: 50. 

“Not to fifty!” Lucifer leapt to his feet to drag Michael away from the controls, but he forced him aside. Castiel shrieked in pain as the Machine pulled the life out of his body in waves of agony. Lucifer and Zachariah cowered in horror as Michael watched with a gleeful smile on his face. 

A few leagues away in the village market place, Sam grabbed Benny’s arm desperately as Castiel’s cries echoed through the air. Villagers stopped and looked around for the source of the terrible sounds, mothers grabbed their children and ran to protect them, but Sam was frozen stock still. 

“Benny, listen! Do you hear that?” Benny nodded, face set into a grimace. “That’s the sound of ultimate suffering. That’s the sound my heart made when Lucifer killed my father. The man in black is making it now.” Benny squinted at him.

“How could you possibly know that?” 

“His true love is marrying someone else tonight. Who else could have a cause for ultimate suffering?” Sam began to push his way through the crowd towards the Thieves’ Forest, but the crowd was too thick. “Excuse me. Pardon me, I have to be somewhere right now. Please, this is life or death!” The crowd refused to part or listen to him. “Benny?” Benny cupped his hands around his mouth.

“EVERYBODY MOVE.” Benny shouted and the throng of people parted like the Red Sea before Moses. Sam grinned at Benny.

“Thank you, my friend.” He dashed through the gap and into the forest. Benny shook his head and followed bemusedly behind his friend. In a small grove of trees not far from the edge of the forest, Benny and Sam came upon a shockingly pale man pushing an empty wheelbarrow deeper into the forest. Sam blocked his path.

“Where’s the man in black?” The man’s eyes widened, but he said nothing. “We can find him in this grove, right?” The man shook his head. “Benny, jog his memory.” Benny wordlessly thumped the man on the head with one massive fist. The man stared at Benny for a moment before he collapsed onto the ground. Sam groaned and rolled his eyes towards the heavens.

“Sorry, Sam. I didn’t mean to jog him that hard.” Benny turned and saw Sam kneeling in the middle of the grove with his eyes shut and his sword clutched tightly in his hands. “Sam?”

“Father.” Sam whispered. “I know that I’ve failed you for the past twenty years, but now you can finally rest. Somewhere close by is a man that can help us, but I can’t find him by myself. I need you. I need your help. I need you to guide my sword. Please.” 

Benny watched Sam rise to his feet and stumble forward like he was pulled by some invisible force. His sword pointed straight out in front of him and wobbled from side to side before it settled with its tip resting just against the trunk of a tree. A soft glow passed over Sam before he gasped and opened his eyes to see the tree. He stared at it for a moment, then thunked his head against the trunk in despair. A door opened in the trunk of the tree. 

“Sam, look.” Benny gasped. They carefully made their way inside, but there was no one there except for a young man with dark hair that lay still on a wheeled table. Sam rushed to the man’s side and undid the straps that bound him to the table. He shook who he decided had to be the man in black, but he didn’t move. Benny gently placed his ear against the man’s chest for a minute, then looked at Sam and shook his head. 

“He’s dead, Sam.” 

“Ha! That’s never stopped a Winchester before. Come on, Benny, help me carry him.” Sam had managed to get the man’s upper body situated before the weight disappeared entirely as Benny lifted him into his arms like a rag doll. 

“Where are we going to take him?” Sam patted his pockets.

“Do you have any money?”

“Just a little.” Sam sighed.

“Hopefully ‘a little’ will be enough to buy us a miracle.


	14. Miracle Max

**Summary for the Chapter:**

> “Don’t rush me, son. You try to rush a miracle man, you end up with a botched miracle. Got any money?” Sam fished in his pockets for the money that Benny had given him.
> 
> “Sixty five.” 
> 
> “Balls, I never worked for so little. Except once, but that was a noble cause.”
> 
> “This is noble! His wife is…crippled, their children are days from starving to death—“
> 
> “Jesus, you’re a shit liar.” Sam tugged at his hair in frustration.
> 
> “I need him to help me avenge my father’s death!” Bobby stopped and stared at Sam, who shifted uncomfortably. It felt like Bobby was looking into his soul.
> 
> “Holy shit. You’re John Winchester’s boy, ain’t ya?”

“You’re sure this is it?” Benny asked. He and Sam stood outside of a small, nondescript cottage in the village. 

“Pretty sure.” Sam knocked on the door to no response. He shrugged and knocked harder.

“Go away!” A gruff voice called out from behind the door. Sam looked a Benny, who shrugged, then continued to knock on the door until a small slot at the top slid to the side. “What do you want?” A pair of bushy eyebrows sat heavily on top of two glaring eyes. 

“You’re the Miracle Man that worked for King Charles for all these years right?” The glare intensified.

“Well I was until the King’s idjit son fired me. Thanks a ton for reminding me, princess. While you’re here, why don’t you come in, give me a big ol’ paper cut and pour lemon juice over it?” The voice spat. “We’re closed!” As soon as the slot was shut, Sam knocked on the door again and nearly landed flat on his face when the door abruptly swung open to reveal a scruffy looking older man. “Get outta here or I’ll call the brute squad!” 

“I’m on the brute squad.” Benny supplied helpfully.

“You _are_ the brute squad.” The man muttered, then tried to close the door, but Sam shoved his foot in the jamb before he could. 

“Please, we need a miracle! It’s important.” The man looked incredulous.

“Look, I’m retired. Why the hell would you want a miracle from someone that the King’s idjit son fired? I just might kill whoever it is you want me to miracle.” Sam shook his head.

“No, he’s dead already.” This perked the man up. 

“Dead already, huh? Bring him in, I’ll look at him.” He opened the door all of the way and gestured to a table in the middle of the room where Benny placed the man in black. “Name’s Bobby, by the way.” Sam nodded as Bobby checked the man in black over, then declared, “I’ve seen worse.” 

“Uh, this is probably going to sound rude…”

“Boy, do I look like I care?” Sam shrugged.

“It’s just that we’re kind of in a hurry.” Bobby didn’t look amused.

“Don’t rush me, son. You try to rush a miracle man, you end up with a botched miracle. Got any money?” Sam fished in his pockets for the money that Benny had given him.

“Sixty five.” 

“Balls, I never worked for so little. Except once, but that was a noble cause.”

“This is noble! His wife is…crippled, their children are days from starving to death—“

“Jesus, you’re a shit liar.” Sam tugged at his hair in frustration.

“I need him to help me avenge my father’s death!” Bobby stopped and stared at Sam, who shifted uncomfortably. It felt like Bobby was looking into his soul.

“Holy shit. You’re John Winchester’s boy, ain’t ya?” Sam was astounded. “I can tell by the stupid look on your face that the answer’s yes.” Bobby started to go back to work on the man in black, then seemed to think of something else. “Where’s your brother, boy?”

“My what?” Now Bobby looked serious. 

“Dean, your brother. John told me he went with your mama to live on that farm in the middle of nowhere, but I always figured that he took you to visit every once in a while!” Bobby shook his head.

“Bobby…my mom died when I was six months old. Dad told me that our house burned down while we were at the market and that she was trapped inside. He never mentioned anybody else, Bobby, he would’ve told me if I had a brother!” 

“Son, believe me when I tell you that your brother is real, and that he’s alive. John told me that when Dean was four years old that Mary told your daddy that she never wanted to see him again and ran off with Dean to a farm in the middle of nowhere. Come to think about it, it would’ve been when you were about six months old…” Bobby trailed off. “Screw it, I don’t want to try and get into that idjit’s head, it’ll just be a pain in the ass for everybody. Either way, your brother is alive. He’s marrying the King’s idjit son tonight.” Sam went white as a sheet.

“No, no, that can’t be right.” 

“Why not?” Sam sank into a chair.

“Because I helped Crowley kidnap him. Crowley never said who he was, just that he was royalty and the job would pay well. I didn’t know that Crowley was planning to kill him until it was too late. You’re sure he’s all right?” Bobby patted him on the shoulder. 

“Trust me, son, he’s fine. And he’ll forgive ya, once you find him again. Neither of you two boys knew. It wasn’t your fault.” Sam buried his face in his hands. “Now, leave me alone so I can get this man back on his feet!” Bobby bustled around the house. “Where’s that bellows cram? I’ll ask him what he thinks he can do for you.”

“Bobby, he’s dead. He can’t answer.” Bobby scoffed.

“Like you know everything. Just so you know, your buddy here is only Mostly Dead. There’s a difference.” He turned to Benny. “Open his mouth. Mostly Dead is still slightly alive. Now, all dead…well with all dead there’s really only one thing you can do.”

“What’s that?” Sam asked and Bobby grinned.

“Go through his pockets for loose change.” Bobby shoved the bellows inside of the man’s open mouth and pushed three pumps of air into what Sam hoped were the man’s lungs. Bobby knocked on the table beside the man’s chest. “Hey! Hey idjit! What’s so important? What’cha got to live for?” Bobby removed the bellows from his mouth and pressed down on the man’s chest. 

For a moment, nothing happened, then the man groaned, “True Love.” And Sam almost fell out of his chair. Bobby, on the other hand, didn’t seem surprised. “Did you hear that?” Sam exclaimed. “True Love! There’s not a more noble cause in the world!” Now Bobby looked uncomfortable.

“Son, True Love is the greatest thing in the world, but that’s not what your man here said.” Sam raised an eyebrow at Bobby. “No, he said ‘to blave’ and everybody knows that ‘to blave’ means to bluff! So he was probably playing cards with somebody, and they killed him ‘cause he cheated.” 

“ _Liar_!” Sam leapt out of his chair so high that he smacked his head into the low ceiling. A woman came tearing down the stairs with a wooden spoon in her hand and flew straight at Bobby. “You dirty, rotten, no good, son of a—“

“Get back, you witch!” Bobby cowered away from her spoon. 

“I’m not a witch, I’m your wife! But after what you just said, I’m not even sure I want to be _that_ anymore!” She kept raining blows down on him with her spoon, but now Bobby dodged around the room to avoid her. 

“You’ve never had it this good!” 

“He said True Love, Bobby, you know he said True Love!”

“Not another word, Ellen!” Now the woman, Ellen, turned to Sam and Benny. 

“He’s just afraid. Ever since Prince Michael fired him, his confidence is shit.” Bobby jolted at the mention of Michael.

“Why’d you say that name?? I told you to never say that name!” Ellen rounded on him. 

“What name? _Michael_?” Ellen taunted.

“Augghhh!” Ellen chased him around the room again and jabbed him between his shoulder blades with her spoon. 

“Michael! Michael Michael Michael _MICHAEL_.” She sang at him and cackled at how uncomfortable he got. 

“I’m not listening!”

“True Love is dying on our kitchen table and you don’t even have the balls to tell them _why_ you won’t help them!!!” 

“Nobody’s hearing nothing!” Bobby insisted with his fingers jammed in his ears. Ellen continued to chase Bobby around the room with her spoon, and Sam decided that he should try to be heard.

“This is…Dean’s…True Love! If you fix him then he’ll stop the wedding tonight!” Bobby grabbed Ellen’s spoon out of her hand which effectively stopped her tirade. 

“If I make this guy better, then Michael suffers?” Sam leaned in and whispered in Bobby’s ear.

“Humiliations galore.” Bobby threw his head back and laughed, then grabbed Ellen and danced her around the room. 

“All right! Gimme the sixty five, and I’ll do it.” Ellen cheered and Sam handed Bobby the money. Fifteen minutes later, Ellen handed him a large chocolate covered pill. Sam looked at it skeptically.

“ _This_ is a miracle pill?”

“The chocolate helps it go down easier, but you have to wait fifteen minutes for potency. Oh, and once he wakes up, he shouldn’t go swimming for at least…how long--?”

“An hour.” Bobby interjected from the corner where he was engrossed in conversation with Benny.

“Yeah, an hour.” 

“Thank you both so much for everything.” Bobby clapped Sam on the shoulder. 

“Make sure you come back and tell me how the King’s idjit son reacts to Dean getting recued, all right?” Sam nodded, motioned for Benny to pick up the man in black, and they left the shop. Bobby and Ellen waved at them from the door as they left.

“Bye-bye boys!” Ellen called.

“Have fun storming the castle!” Ellen leaned closer to Bobby.

“D’you think it’ll work?” She asked under her breath.

“It’d take a miracle.” Bobby muttered, then they resumed their waving.


	15. The Man in Black

**Summary for the Chapter:**

> “How long do we have to wait before it works?” 
> 
> “Your guess is as good as mine.” Sam bit back a shriek as the man in black’s eyes snapped open and he sucked in a gasp of air.
> 
> “I’ll beat you each apart! I’ll take you both together--!” Benny clapped a hand over the man in black’s mouth to stop his rant. 
> 
> “I guess not very long, then.”

Benny and Sam carried the man in black to the bridge across from the castle gate. “Sam!” Benny hissed. “There’s a lot more than thirty men at the gate.” Sam shrugged and plopped down with his back to the stone wall of the bridge and gestured for Benny to put the man in black down beside him.

“It doesn’t make difference now that we have him.” Sam maneuvered the man’s head into an upright position with one hand and pried his mouth open with the other. “Come help me with this, Benny. We’re gonna have to force feed him the pill.” Benny pulled a pouch that contained the pill out of his pocket.

“Do you think it’s been fifteen minutes?” Sam shook his head.

“I doubt it, but we can’t afford to wait. The wedding’s in half an hour. We have the best chance of success if we strike in the hustle beforehand. Tilt his head back.” Benny obliged and handed Sam the pill. He kissed it, then pushed it into the man in black’s mouth and stroked his throat until he felt it go down.

“How long do we have to wait before it works?” 

“Your guess is as good as mine.” Sam bit back a shriek as the man in black’s eyes snapped open and he sucked in a gasp of air.

“I’ll beat you each apart! I’ll take you both together--!” Benny clapped a hand over the man in black’s mouth to stop his rant. 

“I guess not very long, then.” Benny looked at the man in black who appeared to be in deep concentration.

“Why can’t I move my arms?”

“You’ve been Mostly Dead all day.” Sam shot Benny a look.

“We had Bobby, the Miracle man make us a pill that would bring you back.” Sam explained. 

“Who are you? Are we enemies? Why am I sitting against this wall? Where’s Dean?” Sam tried to answer each question as it came, but the man in black spat them out too quickly for him to get a word in edgewise. 

“Let me explain.” Sam thought for a moment. “Nope, no time. Let me summarize: Dean’s going to marry Michael in a little more than half an hour. All we have to do is get in, stop the wedding, steal the prince and make our escape after I kill Lucifer.” The man in black’s thumb twitched against his chest.

“That doesn’t give us much time to fool around.” Benny looked ecstatic.

“You wiggled your finger!” Benny plowed on despite Castiel’s withering look. “That’s wonderful, cher!” 

“I’ve always been a quick healer. What are we up against?” 

“There’s only one way in,” Sam hefted the man in black up so that he could look over the wall at the gate. “And it’s guarded by…” Sam quickly counted the soldiers. “…sixty men.”

“And what do we have at our disposal?” 

“Your brains, Benny’s strength, and my steel.” Castiel blinked at Sam.

“That’s it? Impossible. I might have been able to come up with something if I’d had a month to plan, but like this…” He flopped his head from side to side. Again, this development in the man in black’s healing made Benny look fit to burst.

“You just shook your head! Doesn’t that make you happy?” This time, Benny did stop as the man in black’s stare. 

“My brains, his steel, and your strength up against sixty armed guards, and you think that a little head jiggle is going to make my day?” Benny shrugged, but he never dropped his smile. “If we only had a wheelbarrow, then maybe we’d have a fighting chance.” Sam perked up.

“Benny, where did we put the wheelbarrow that guy in the woods had?” Benny thought for a moment.

“I think we put it over the guy in the woods.” Castiel groaned.

“Why didn’t you mention that with the things we have at our disposal? Now what would really sell it is a holocaust cloak.” Benny pulled a swath of black fabric out of his bag.

“Will this work?” Sam gaped at him.

“Where the hell did you get that?”

“At Bobby’s. We got to talking while Ellen was working on the pill, and when I tried it on, it fit me so well that he said I could have it.” The man in black cleared his throat.

“Yes, yes, wonderful, excellent. Help me up, please.” Sam and Benny hefted an arm each over their shoulders and helped the man in black to his feet. “I’ll need a sword sooner or later.” 

“You can hardly stand! What do you need a sword for?” Castiel’s head fell backwards and Benny lifted it up. 

“Nobody else knows that, now do they?” This time his head fell against his chest, and again, Benny lifted it back up, but this time he left his hand on the nape of his neck for support. “Thank you…what’s your name?” Benny smiled.

“Benny. And this is—“Benny gestured to Sam.

“Sam. I know.” Sam rubbed at the back of his neck. 

“So you do remember that, then.” The man in black gave him a feeble nod. 

“Dean told me about you. He thought you were dead, Sam.” Sam looked up at him. 

“What? He knew about me? I just found out about him earlier today.” The man in black looked crushed. 

“He said that your father told your mother that you had been killed, then he disappeared.” Sam tugged on his hair. 

“Gods, this is so messed up.” Castiel hummed in agreement. 

“Now that we know how we’re getting in, we need to talk about what might happen once we get inside. That could be an even bigger challenge.”

“I’ll say. How do I find Lucifer? Once I find him, how will I find the two of you again? Once I find you again, how will we escape?” Benny saved the man in black from Sam and turned his head into his massive chest.

“Leave him alone, cher, he’s had a hard day.” Benny turned his head back front.

“Right. Sorry about that…I just realized that I have no clue what your name is.” The man in black attempted a shrug.

“That might be a good thing.” Sam huffed.

“Well I can’t keep calling you ‘the Man in Black’, can I?” He laughed, then winced.

“’The Man in Black’? I actually like that. But, if you must know, my name is Castiel.” Sam nodded, then they began their descent towards the gate.

“Sam?” Benny whispered.

“Yeah, Benny?”

“I really hope we win.”


	16. The Wedding

**Summary for the Chapter:**

> “Mawwage. Mawwage is what bwings us togevah today.” Dean had to stifle a chuckle at the man’s voice. “Mawwage, that bwessed awwangement, that dweam wifin a dweam.” Shouts and crashes could be heard from outside and Dean turned to look at the doors.
> 
> “Stand your ground, men, stand your ground!” Dean heard Captain Milligan shout. Outside the gates, Benny’s head was just visible over the wall, partly covered by the holocaust cloak.

**Notes for the Chapter:**

> Okay, so I couldn't think of a replacement for the Impressive Clergyman from the movie, so that who it is. Hopefully the way I misspelled the words on purpose conveys his speech pattern correctly.

Despite the trails of disgust that ran through his body as Michael looked him over in all of his wedding finery and presented him with a delicate silver choker necklace that he insisted he put on Dean himself, Dean was perfectly calm. Michael picked up on this and commented on it.

“You don’t seem too excited, dearest.” Dean shrugged.

“Should I be?” Michael leered at him.

“I’m told that people often are on their wedding day.” Dean laughed.

“This isn’t my wedding day. Castiel’s going to save me.” Michael patted his hand condescendingly and followed him out of the room.

That same moment, outside of the castle gate, Sam, Benny, and Castiel, who still had to lean his weight against Benny were about to begin their attack. Sam held out his hand, Benny placed his on top, and after a momentary struggle, Castiel managed to flop his arm on top of theirs. The three men nodded at each other, then set to work.

Within the cathedral, an impressive looking clergyman gestured for Dean and Michael to approach him. When the two men had reached him, he cleared his throat and turned to address the crowd.

“Mawwage. Mawwage is what bwings us togevah today.” Dean had to stifle a chuckle at the man’s voice. “Mawwage, that bwessed awwangement, that dweam wifin a dweam.” Shouts and crashes could be heard from outside and Dean turned to look at the doors.

“Stand your ground, men, stand your ground!” Dean heard Captain Milligan shout. Outside the gates, Benny’s head was just visible over the wall, partly covered by the holocaust cloak. 

“I am the Dread Pirate Roberts!” Benny shouted. Castiel had told him to accentuate his drawl so that he would be that little bit more difficult to understand. Castiel assured him that this would scare the pants off the guards. “There will be no survivors!” Castiel leaned heavily on Sam’s back as he pushed the wheelbarrow that Benny stood on. 

“Now?” Sam wheezed from the strain. 

“Not yet.”

“My men are here! I am here. But soon…you will not be here.” Benny pointed at the guards in front of the gate, who had begun to quake in their positions.

“Now?” Same begged. Castiel nodded.

“Light him.” Sam grabbed a torch from a holder on the side of the wheelbarrow and lit Benny’s cloak on fire. The guards screamed and began to scatter. 

“The Dread Pirate Roberts takes no survivors! All of your worst nightmares are about to come true!” More soldiers ran from Benny’s flaming form in terror.

Back inside the cathedral, the clergyman had continued with his speech as though everything was fine. “And wove, Twue Wove, wiww, fowwow you fowevah—“Michael shot a look at Lucifer, who exited the cathedral along with his triple of soldiers.

“The Dread Pirate Roberts is here for your souls!” The few soldiers that still remained at the gate with Captain Milligan turned and fled. 

“Stay where you are!” Captain Milligan screamed. “Fight, you cowards! Stay where you are!”

“So tweaswe your wove—“Michael had enough.

“Skip to the end.” He bit out through clenched teeth. The clergyman looked shocked.

“Have you the wing?” Michael grabbed Dean’s hand, but Dean’s gaze was fixed on the doors and a wide smile graced his lips.

“It’s Cas. He’s here for me.” 

“Benny, grab the portcullis!” Sam shouted, and Benny managed to grab it inches before it hit the ground and force it back up. Captain Milligan was now the only thing that stood between them and the castle.

“Your ‘Cas’ is dead. I killed himself.” Michael gloated.

“Then why do you look so scared?”

Sam pulled the burning cloak off of Benny, who had taken Castiel off of his hands. “Give us the gate key.” Sam demanded.

“What gate key?” Sam smirked and looked at Benny.

“Benny? Tear his arms off.”

“Oh, you mean this gate key!” Captain Milligan held up a small pouch and handed it over to Sam before he turned tail and fled. 

“And do you, Pwince Dean—“

“Man and wife, say man and wife!” Michael hissed.

“Man and wife.” The astonished clergyman pronounced. Michael shoved Dean at King Charles and Queen Rebecca. 

“Take him to the honeymoon suite. I’ll be there shortly.” King Charles tenderly threaded Dean’s arm through his own, but Dean’s heart was so shattered that he didn’t notice. 

“He didn’t come.” 

\---OoO---

Lucifer raced down the hall towards the castle gate with his triple, but it was too late. Sam, Benny, and Castiel stood waiting for him. Lucifer sighed inwardly. “Kill the dark one and the giant, but leave the tall one to me for…questioning.” His triple sprung to follow his orders and were quickly killed or incapacitated by Sam. He stepped forward and looked Lucifer in his eyes.

“Hello. My name is Samuel Winchester. You killed my father. Prepare to die.” Lucifer nodded, then bolted around the corner and out of sight. Sam raced after him but was quickly stopped when Lucifer ducked inside a room and locked the door behind him. Sam tried to force it open, but it wouldn’t budge. “BENNY! Benny, please help me! I need your help!” Sam roared. Benny looked down at Castiel, who was still too weak to stand.

“I can’t leave him alone!” 

“He’s getting away from me, Benny! _Please_!” Benny sighed and wrapped Castiel’s arms around a suit of armor. 

“I’ll be right back.” He found Sam nearby and shoved the door off its hinges with one hand.

“Thank you.” Sam panted, then rushed into the room. 

A few halls down, King Charles and Queen Rebecca escorted Dean to the honeymoon suite. “What an odd wedding.” King Charles commented.

“Yes, very odd. Come along, dears.” She walked ahead of Dean, so he and King Charles were alone when Dean suddenly stopped. He leaned down and kissed the king’s wrinkled cheek. King Charles looked at him in shock.

“What was that for?” Dean gave him a sad smile.

“Because you’ve always treated me kindly. And because I’ll never see you again, and because I don’t want you to blame yourself when I kill myself once we reach the honeymoon suite.” King Charles patted his arm. 

“Won’t that be lovely?” Dean’s heart broke that the king was so far gone in his old age. When they had caught up with Queen Rebecca, King Charles elbowed her in the side. “He kissed me!” Queen Rebecca smiled at them. She opened the door in front of them to the honeymoon suite. She patted Dean on the cheek, then left with King Charles.   
Dean didn’t spare a glance for the sumptuously decorated room. He only had eyes for the bejeweled case on the windowsill. He opened it and took out a silver dagger. He placed it over his heart, took in a deep breath, and—

“There’s a shortage of perfect chests in this world. It’d be a shame to damage yours.” And turned to see Castiel, still in his Roberts clothes, draped on the bed. 

“Cas!” Dean rushed over to the bed, threw himself on top of Castiel, and peppered his face with little kisses. “Cas, Cas, _Cas_. Cas, are you okay? Why won’t you hold me?” 

“Gently.” Castiel breathed as Dean’s kisses moved lower to his throat and his hands came up to bring Castiel’s face closer to his. 

“That’s all you can say right now? ‘Gently?’” Dean tugged him up further and Castiel squeaked in pain.

“Gently!” He begged. Dean dropped his head abruptly, which smacked into the headboard. “Ow.”

\---OoO---

Sam rounded a corner and found Lucifer cornered in a large banquet room. Lucifer, it seemed, had been ready for Sam to find him, and he launched a small dagger at Sam, which hit the center of Sam’s stomach. All of the wind rushed out of his lungs and he fell against the wall behind him. “I’m sorry, Dad.” Sam gasped. “I tried. I tried.” Understanding dawned in Lucifer’s eyes.

“Now I see. You’re that little common brat that I taught a lesson to all those years ago. Incredible. And you’ve worked your whole life just to fail now? That has to be the worst thing I’ve ever heard. Perfect.” Sam slumped to the ground. Lucifer made it all the way to the door, when he heard a scuffle behind him. He turned to watch Sam struggle to stand.

“My God. Are you still trying to win?” Sam took a step forward, then staggered back against the wall again. Lucifer tutted. “You have an overdeveloped sense of vengeance. It’ll get you into trouble someday, you know.” Lucifer drew his sword and thrust at Sam, but he parried it easily. Confused, Lucifer aimed two more blows which were also deflected. 

“Hello. My name is Samuel Winchester. You killed my father. Prepare to die.” He managed to advance a few steps on Lucifer then collapsed against a table. Lucifer struck at him and this time Sam’s block almost grazed his arm. “Hello. My name is Samuel Winchester. You killed my father. Prepare to die.” Lucifer’s strikes became more desperate as Sam regained his strength and began to fight back. He lunged forward at Lucifer. “Hello! My name is Samuel Winchester. You killed my father prepare to die.”

“Stop saying that!” Lucifer growled. Sam managed to get two blows in to Lucifer’s shoulders. He staggered backwards towards one wall as Sam forced him to retreat further and further until he had nowhere else to run.

“ _Hello! My name is Samuel Winchester! You killed my father! Prepare to die_!” Sam had him pinned against the long table up against one wall.

“No!” Lucifer shrieked!

“Offer me money!” Sam slashed a jagged cut on Lucifer’s left cheek.

“Yes!”

“And power too. Promise me that!” And another, on his right.

“Everything I have and more!” Lucifer swore. “Please.” Sam took a step back and spread his arms.

“Offer me whatever I ask for.”

“Whatever you want. Anything you want!” Lucifer pleaded. Sam grinned, but there was no joy in his life. In a flash, Sam sprang forward and buried his sword up through Lucifer’s ribs and into his heart.

“I want my father back, you son of a bitch.” A trail of blood escaped Lucifer’s mouth. Sam wrenched his blade inside of Lucifer, then pulled it out. Lucifer collapsed at his feet, dead. And John Winchester smiled.


	17. To The Pain

**Summary for the Chapter:**

> “It never happened.” Dean shook his head.
> 
> “But it did, Cas, I was there! The priest said ‘man and wife.’” Castiel managed a smirk.
> 
> “Did you say ‘I do’?” Dean thought for a moment.
> 
> “Uh, no, he kinda skipped that part.” Castiel’s fingers twitched and Dean laced his own through them.
> 
> “Then you’re not married. If you didn’t say it, then you didn’t do it.” Castiel’s gaze shifted to the doorway. “Don’t you agree, your Highness?” Dean whipped his head to see Michael at the door with his sword drawn.

Dean had moved off of Castiel and laid curled up against his side while Castiel filled him in on what had happened to him after the Fire Swamp. Dean’s heart clenched when Castiel talked about the Machine and it took every ounce of his willpower to keep himself from clutching Castiel tighter while he was still weak. Then Dean remembered that wedding and guilt flooded him. 

“Cas, will you ever be able to forgive me?” Castiel tried to tilt his head but all he managed to do was flop it to one side. 

“Why would I need to forgive you? Have you committed some hideous sin lately that I don’t know about?” Dean ducked his head.

“I got married. I didn’t want to, I swear! It just happened so fast—“

“Never happened.” Dean snapped his head up to meet Castiel’s eyes.

“What?”

“It never happened.” Dean shook his head.

“But it did, Cas, I was there! The priest said ‘man and wife.’” Castiel managed a smirk.

“Did you say ‘I do’?” Dean thought for a moment.

“Uh, no, he kinda skipped that part.” Castiel’s fingers twitched and Dean laced his own through them.

“Then you’re not married. If you didn’t say it, then you didn’t do it.” Castiel’s gaze shifted to the doorway. “Don’t you agree, your Highness?” Dean whipped his head to see Michael at the door with his sword drawn. 

“That’s a minor technicality that I’ll be sure to fix soon. But first things first,” He pointed his sword at Castiel. “To the death.”

“No!” Castiel shouted and Michael paused. “To the pain.” 

“I’m not familiar with that phrase.” Michael challenged and Castiel met his gaze with eyes full of fire. 

“Don’t worry, I’ll explain, and I’ll make sure to use smalls words so you can understand me, you assbutt.” Michael’s eyes almost popped out of their sockets. 

“That has to be the first time anyone had ever dared to insult me.” 

“It won’t be the last. ‘To the pain’ means that the first thing you’ll lose will be your feet, just below the ankles, then your hands at the wrists, and then your nose.” 

“And then my tongue, I assume? I must’ve killed you too quickly last time, but I’ll take my time with you now.” Michael readied himself to charge, but Castiel stopped him.

“I wasn’t finished! Next you’ll lose your left eye followed by your right.” Michael sighed.

“And then my ears, I get it! Let’s get on with it.”

“Wrong!” Michael flinched. “You’ll get to keep your ears and this is why: so that every shriek of every child at seeing your hideousness will be yours to cherish. Every babe that weeps at your approach, every woman who cries out ‘Dear God, what is that thing?’ will echo in your perfect ears. _That_ is what ‘to the pain’ means. It means that I leave you in anguish to wallow in freakish misery. Forever.” It took Michael several seconds before he was able to respond. 

“I think you’re bluffing.” Castiel laughed.

“It’s a possibility, pig. I might be bluffing. It’s conceivable, you miserable vomitous mass. I’m only lying here because I don’t have the strength to stand.” He shifted his eyes over to Dean and suddenly they were warm and loving. “Then again…maybe I have the strength to stand after all.” 

Dean watched in awe as Castiel raised his torso off the bed, swung his legs over the side, and gracefully rose to his feet and pulled himself up to his full height as he pointed his sword at Michael’s throat. 

“Drop. Your. Sword.” Castiel’s demand was met with the sound of metal clattering against stone and Michael’s sword fell from his limp fingers. “Have a seat. Would you tie him up for me, Beloved? And make it as tight as you’d like.” Dean was happy to oblige and reveled in Michael’s pained grunts as he bound him to the chair. Dean was still occupied with Michael when Sam rushed into the room. 

“Where’s Benny?” Castiel shrugged.

“I don’t know, I thought he was with you!” 

“Nope.” 

“Well in that case—oh.” Castiel’s knees buckled underneath him and he fell against the bedpost. Sam knelt beside Dean and took over for him.

“Help him.” Dean helped Castiel lay back on the bed, but his eyes never left Sam.

“Why does he need help?” 

“Because he still has no strength.” Michael shouted in triumph.

“I knew it! I knew you were bluffing! I knew he was…bluffing.” He quailed as Sam brandished his sword in Michael’s face. 

“Want me to take care of this thing for you?” Castiel shook his head.

“Thanks, but no. No matter what happens to us, I want him to live the rest of his life alone with his cowardice.” Sam reluctantly sheathed his sword.

“Sam!” A deep voice called from below the open window. Sam rushed over while Dean helped Castiel limp to the window so that he could see who was there. “There you are, brother! I saw four white horses in the stables over there, and I thought, there will be four of us if we manage to find the Prince.” Benny turned and saw Dean at Castiel’s side. He waved up at Dean. “Hello!” Dean waved back. “So I took the horses with me just in case we ran into each other again. I guess we just did.” Sam grinned.

“Benny, you’re a genius!” Even in the dark, Dean swore that he saw a flush stain Benny’s cheeks, but he shook it off and held out his arms. Dean raised his eyebrows and looked at Sam, who nodded at him. Dean draped Castiel’s arm over Sam’s shoulder and leapt out the window into Benny’s arms. The breath left Castiel’s lungs at the stunning image Dean made with his silver cape streaming out behind him. Benny set Dean down on his feet and held out his arms for Sam. 

“You know, it’s kinda weird.” Sam commented. “I’ve been in the revenge business for so long. Now that it’s over…I have no clue what I’m gonna do with my life now.” Castiel hummed and flopped his hand onto Sam’s shoulder.

“Ever considered piracy?” Sam gave him an incredulous look. “You’d make a great Dread Pirate Roberts, you know.” Sam nodded at Castiel just as he began to tumble out the window. Fortunately, Benny was prepared and caught him with ease and passed him over to Dean. By the time Dean had gotten Castiel situated on his own horse, which Castiel assured him that he could ride, Sam had made it to the ground and onto his own horse. 

They rode to freedom. Castiel led them to Roberts’ ship in the harbor and went over the procedure with Sam. Dean wasn’t excited about having Castiel away from him for three weeks so soon after getting him back, and even less excited about seeing Sam go, but he knew that it was important for both of them. When Sam, Castiel, and Benny were ready to leave, Dean pulled Sam to the side.

“So…” Dean didn’t know where to start. He stammered for a second, then cleared his throat. “I guess, uh…Dad lied. To you and Mom. And now he’s dead.” Sam nodded. “Geez. I always knew that Mom had problems with him, but she never said why. Guess this pretty much sums it up, then.” Sam chuckled.

“So uh, where…where does that leave us?” Dean shrugged.

“I really don’t know, Sammy. I mean, _Roberts_.” Sam rolled his eyes. “The best thing to do is probably just see how things go. Y’know, make sure you come visit me and Cas every once in a while, whenever you’re nearby. And, y’know…whenever you decide you wanna settle down, Cas is a pretty fair builder. We can set you up by us, if you want.” Sam patted Dean on the shoulder. 

“Let’s see how the whole ‘pirate’ things works out for me first, huh?” Dean nodded and pulled Sam into a fierce hug. “I’m gonna miss you, jerk.” Sam’s voice was muffled into Dean’s shoulder.

“I’m gonna miss you too, bitch.” Sam pulled back and Dean noticed the tears in his little brother’s eyes. “Take care of Cas for me, you hear?” Sam nodded and slapped Castiel on the back as he made his way onto his new ship. Castiel joined Dean a short ways from the pier. As the sun rose over the water, they knew they were safe. A powerful wave of love swept over them, and as they reached for each other, they knew that nothing would ever separate them again. Castiel pulled Dean in for a kiss and Dean responded eagerly.

Since the invention of the kiss, there have been five kisses that were rated the most passionate, the most pure. This one left them all behind. Dean pulled back and rested his forehead against Castiel’s. 

“You better come home safe this time.” Castiel stroked his thumbs across Dean’s cheeks. 

“I promise, my love, I will come home to you.” Dean pressed one more kiss to Castiel’s lips, then nudged him towards the ship. 

“Go on, Cas. The Dread Pirate Roberts doesn’t like to be kept waiting.” There were tears in their eyes, but they smiled at each other as Castiel boarded the ship. Dean didn’t leave the pier until the ship was completely out of sight on the horizon. He wiped the tears from his cheeks and turned towards home. 

“See you in three weeks, Cas.”


End file.
